2002 Tax Help Archives  
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General Procedural Questions

This is archived information that pertains only to the 2002 Tax Year. If you
are looking for information for the current tax year, go to the Tax Prep Help Area.

How long do I need to keep certain records?

Records such as receipts, canceled checks, and other documents that prove an item of income or a deduction appearing on your return should be kept at least until the statute of limitations expires for that return. Usually this is three years from the date the return was due or filed, or two years from the date the tax was paid, whichever is later. There is no period of limitations when a return is false or fraudulent or when no return is filed. You should keep some records indefinitely, such as property records, since you may need them to prove the amount of gain or loss if the property is sold. For more details, refer to Publication 552 (PDF), Recordkeeping for Individuals, or Tax Topic 305 on Recordkeeping.

If you are an employer, you must keep all your employment tax records for at least four years after the tax is due or paid, whichever is later. For additional information, refer to Publication 583 (PDF), Starting a Business and Keeping Records. People in business often have expenses for travel, entertainment, and gifts. The documentation you should keep for each of these expenses can be found in Publication 463 (PDF), Travel, Entertainment, Gift and Car Expenses.

References:

9.4 Estimated Tax: Large Gains, Lump-sum Distributions, etc.
If I anticipate a sizable capital gain on the sale of an investment during the year, do I need to make a quarterly estimated tax payment during the tax year?

If you first receive income subject to estimated tax during a period other than the first quarter, you must make your first payment by the due date for the period the income is received. You can pay your entire estimated tax by the due date for the period the income is received, or you can pay it in installments by the due date for that period and the due dates for the remaining periods.

If you are making estimated tax payments you can increase your quarterly estimated tax payments or increase your Federal income tax withholding to cover the tax liability. If you have the proper amount withheld you may not be required to make estimated tax payments nor have to file Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts, with your tax return (as you would if you just increased the remaining estimated tax payments). If you wait and make increased estimated tax payment in the later quarters, you would have to file Form 2210 with your tax return because we do not know when you received the income. Since you really did not receive the income evenly throughout the year, you have to tell us when the income was received by filing Form 2210.

References:

If I sell stock at a gain, do I pay estimated taxes on the entire profit when the next quarterly payment is due or can I divide it by the number of quarterly payments left for the year and make these equal payments at each subsequent quarter?

If you first receive income subject to estimated tax during a period other than the first quarter, you must make your first payment by the due date for the period the income is received. You can pay your entire estimated tax by the due date for the period the income is received, or you can pay it in installments by the due date for that period and the due dates for the remaining periods.

References:

On December 20, I received a large mutual fund distribution. Due to the large distribution I'm going to owe $7,000 when I file my return. Is it okay to just pay the $7,000 when I file my return?

If the $7,000 in tax is a result of a distribution not covered by prepayments of tax, either through income tax withholding or estimated tax payments, you should make an estimated tax payment by January 15th of the next year. If you wait to pay the $7,000 with your return, you may be penalized for an underpayment of estimated taxes. Even if you make an adequate payment of tax by January 15th, you may be assessed an estimated tax penalty by the IRS service center when your return is processed unless you file Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts . This is because estimated tax payments are normally made in four equal installments and the IRS will not know your liability occurred in the fourth quarter unless you explained when the income was received.

You may be subject to the penalty if you owe at least $1,000 in tax after subtracting your withholding and credits from your tax liability, and you did not prepay at least 90% of your current year's tax or 100% of your previous year's tax. (The latter percentage is higher for higher-income taxpayers with adjusted gross incomes from the previous year of more than $150,000.)

If you make an adequate payment by January 15th but made no earlier estimated tax payments, use Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts, to compute your penalty. Check the box on the front page selecting the Annualized Income Installment method, and then complete Schedule AI on page 3. When you compute the penalty on page 2 of that form using the numbers from Schedule AI, your penalty will be $0 if you made an adequate payment. Even if you did not make the January 15th payment or made an adequate payment, the annualized income method on Form 2210 may significantly reduce the estimated tax penalty.

For more information on estimated tax payments and the underpayment of estimated tax penalty, refer to Publication 505 (PDF), Tax Withholding and Estimated Tax.

References:

  • Publication 505 (PDF), Tax Withholding and Estimated Tax
  • Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts

10.1 Captial Gains, Losses/Sale of Home: Property (Basis, Sale of Home, etc.)
I lived in a home as my principal residence for the first 2 of the last 5 years. For the last 3 years, the home was a rental property before selling it. Can I still avoid the capital gains tax and, if so, how should I deal with the depreciation I took while it was rented out?

If, during the 5-year period ending on the date of sale, you owned the home for at least 2 years and lived in it as your main home for at least 2 years, you can exclude up to $250,000 of the gain ($500,000 on a joint return in most cases). However, you cannot exclude the portion of the gain equal to depreciation allowed or allowable for periods after May 6, 1997. Since you cannot exclude all of the gain, report the entire gain realized on Form 1040, Schedule D (PDF) line 8. Report the amount of exclusion you qualify for on the line directly below the line on which you report the gain. Write Section 121 exclusion in column (a) of that line and show the amount of the exclusion in column (f) as a loss (in parentheses).

For additional information on selling your home, refer to Publication 523 (PDF), Selling Your Home.

References:

10.2 Captial Gains, Losses/Sale of Home: Stocks (Options, Splits, Traders)
How do I figure the cost basis of stock that has split, giving me more of the same stock, so I can figure my capital gain (or loss) on the sale of the stock?

The basis of the old shares must be allocated to the old and new shares in proportion to the fair market value of each on the date of the split. Thus, you generally divide the adjusted basis of the old stock by the number of shares of old and new stock. The result is your new basis per share of stock. If the old shares were purchased in separate lots for differing amounts of money, the adjusted basis of the old stock must be allocated between the old and new stock on a lot by lot basis.

References:

How do I calculate the cost basis of the shares that have split and are later sold from my employee stock purchase plan?

You need to determine what your basis is in the company stock on the date of the split. The new shares assume part of your basis in the company stock on that date. You must divide the adjusted basis in the old stock by the number of shares of old and new stock. The result is your basis for each share of stock.

For example, if you owned two shares of company stock with a basis in one at $30 and the other $45, and the company declares a three for one stock split, you now have six shares of stock. Three of the shares will have a basis of $10, and three will have a basis of $15.

Because this is an Employee Stock Option Plan, you may have to report some or all of the gain on the sale of this stock as ordinary income (wages).

References:

Would shares in mutual fund acquired through dividend reinvestment in prior years be long-term capital gains while shares acquired through dividend reinvestment in the year of sale be treated as short-term capital gains?

Any shares or fractional shares purchased and sold during the current tax year are short-term capital assets. For shares purchased in the year previous to the tax year to be considered long-term, the holding period must be more than one year.

References:

Can I take a long-term capital loss (up to the $3,000 limit) against my ordinary income without any long-term capital gain?

Yes. The $3,000 capital loss limitation refers to how much net capital loss can offset ordinary income on your tax return.

For more information on capital gains and losses and capital loss carryovers, refer to Chapter 4 of Publication 550 (PDF), Investment Income and Expenses.

References:

Can I use a long-term capital loss carried over from a prior year to offset a short-term capital gain?

A loss carryover maintains its character as long-term or short-term and must first be used against gains, if any, in its own category, but can then offset net gains from the other category, as well as up to $3,000 of ordinary income. If, for example, your only gain or loss is the long -term capital loss carryover, then line 17 of Form 1040, Schedule D (PDF), which nets the net short-term gain or loss against the net long-term gain or loss, will apply your loss carryover against your short-term gain. After that, any remaining net loss will be allowable as a deduction against up to $3,000 of your ordinary income. The remainder will be available to be carried over to the following year as long-term loss.

References:

Can I use a long-term capital loss to offset a short-term capital gain before using it to offset a long-term gain?

No, long-term capital gains and losses must first be combined to arrive at net long-term gain or loss before the result can be netted against the net short-term gain or loss. If you follow the Form 1040, Schedule D (PDF), Capital Gains and Losses, Parts 1 and 2, line-by-line, the form will perform the netting for you in this order.

References:

Can short-term capital gains be offset with long-term capital losses?

Before a loss from one category, short or long term, can offset gain from the other category, the losses and gains from each category must be combined to arrive at a net gain or loss from that category. Then, the net gain or loss from each category is combined.

When you carry a capital loss over to the following year, it retains its character as long-term or short-term and must be first combined with the other entries in its category.

Refer to Reporting Capital Gains and Losses in Publication 550 (PDF), Investment Income and Expenses.

References:

How do I determine my gain or loss on the proceeds reported on Form 1099-B from a short sale entered into last year if I have not yet bought the stock to deliver back to my broker?

In general, you cannot determine your gain or loss until you purchase the stock that you are going to deliver to close the short sale. You still need to report the gross proceeds on Schedule D so that the total of lines 3 and 10, column (d), reconciles with all of your Forms 1099-B.

Also, in columns b and c write "short sale." In column f, write "see attached statement." In the statement, explain the details of the short sale and that it is not closed. Include your name as it appears on your return and your social security number.

For more information on rules and exceptions that may apply, refer to Chapter 4 of Publication 550 (PDF), Investment Income and Expenses.

References:

Do I need to pay taxes on that portion of stock I gained as a result of a split?

No, you generally do not need to pay tax on the additional shares of stock you received due to the stock split. You will need to adjust your per share cost of the stock. You overall cost basis has not changed, but your per share cost has changed.

You will have to pay taxes if you have gain when you sell the stock. Gain is the amount of the proceeds from the sale, minus sales commissions, that exceeds the adjusted basis of the stock sold.

References:

I buy and sell stocks as a day trader using an online brokerage firm. Can I treat this as a business and report my gains and losses on Schedule C?

A business is generally an activity carried on for a livelihood or in good faith to make a profit. Rather than being defined in the tax code, exactly what activities are considered business activities has long been the subject of court cases. The facts and circumstances of each case determine whether or not an activity is a trade or business. Basically, if your day trading activity goal is to profit from short-term swings in the market rather than from long-term capital appreciation of investments, and is expected to be your primary income for meeting your personal living expenses, i.e. you do not have another regular job, your trading activity might be a business.

If your trading activity is a business, your trading expenses would be reported on Form 1040, Schedule C (PDF), Profit or Loss from Business (Sole Proprietorship) instead of Form 1040, Schedule A (PDF), Itemized Deductions. Your gains or losses, however, would be reported on Form 1040, Schedule D (PDF), Capital Gains and Losses, unless you file an election to change your method of accounting.

If your trading activity is a business and you elect to change to the mark-to-market method of accounting, you would report both your gains or losses on Part II of Form 4797 (PDF), Sales of Business Property.

A change in your method of accounting requires the consent of the Commissioner and can not be revoked without the consent of the Commissioner. Though there is no publication specific to day traders, the details for traders information for securities and commodities is covered in Internal Revenue Code Section 475(f) and Revenue Procedure 99-17 and Rev. Proc. 99-49.

References:

Is there any publication that explains the proper way to file a Schedule C as a day trader?

Publication 550 (PDF), Investment Income and Expenses, which is specific to traders, includes a section titled Special Rules for Traders in Securities.

Internal Revenue Code section 475(f) and Revenue Procedure 99-17 apply only to traders who elect to use mark-to-market method of Accounting.

References:

  • Publication 550 (PDF), Investment Income and Expenses
  • Publication 535 (PDF), Business Expenses
  • Form 3115 (PDF), Application for Change in Accounting Method
  • Internal Revenue Code section 475(f)
  • Revenue Procedure 99-17

I have expenses associated with my day trading business, but I am unsure about how to report my gains and losses. How do I file as a day trader and how do I use the mark-to-market accounting method?

Special rules apply if you are a trader in securities in the business of buying and selling securities for your own account. To be engaged in business as a trader in securities, you must meet all the following conditions.

  • You must seek to profit from daily market movements in the prices of securities and not from dividends, interest, or capital appreciation
  • Your activity must be substantial.
  • You must carry on the activity with continuity and regularity.
The following facts and circumstances should be considered in determining if your activity is a securities trading business.
  • Typical holding periods for securities bought and sold
  • The frequency and dollar amount of your trades during the year.
  • The extent to which you pursue the activity to produce income for a livelihood.
  • The amount of time you devote to the activity.

If your trading activity is a business, your trading expenses would be reported on Form 1040, Schedule C (PDF), Profit or Loss from Business (Sole Proprietorship) instead of Form 1040, Schedule A (PDF), Itemized Deductions. Your gains or losses, however, would be reported on Form 1040, Schedule D (PDF), Capital Gains and Losses, unless you file an election to change your method of accounting.

If you qualify for and elect to change to the mark-to-market method of accounting, you would report both your gains or losses on Part II of Form 4797 (PDF), Sales of Business Property.

The mark-to-market method of accounting cannot be revoked without the consent of the Secretary. Though there is no publication specific to day traders, the details for traders in securities and commodities are covered in Internal Revenue Code section 475(f) and Revenue Procedure 99-17.

If you elect to use the mark-to-market method of accounting, a security that you hold at the end of the tax year will generally be treated as sold at its fair market value on the last business day of the tax year. Any gain or loss must be recognized. That gain or loss is taken into account as an adjustment in figuring your gain and loss when you later dispose of the security. See Publication 550 (PDF), Investment Income and Expenses, for general information on mark-to-market accounting rules.

References:

  • Publication 535 (PDF), Business Expenses
  • Publication 550 (PDF), Investment Income and Expenses
  • Form 3115 (PDF), Application for Change in Accounting Method
  • Form 4797 (PDF), Sales of Business Property
  • Internal Revenue Code Section 475(f)
  • Revenue Procedure 99-17

I am a day trader. How do I go about paying tax on the gain as a business and not on Schedule D?

Special rules apply if you are a trader in securities in the business of buying and selling securities for your own account. To be engaged in business as a trader in securities, you must meet all the following conditions.

  • You must seek to profit from daily market movements in the prices of securities and not from dividends, interest, or capital appreciation.
  • Your activity must be substantial.
  • You must carry on the activity with continuity and regularity.

The following facts and circumstances should be considered in determining if your activity is a securities trading business.

  • Typical holding periods for securities bought and sold.
  • The frequency and dollar amount of your trades during the year.
  • The extent to which you to produce income for a livelihood.
  • The amount of time you devote to the activity.

If your trading activity is a business, your trading expenses would be reported on Form 1040, Schedule C (PDF), Profit or Loss from Business (Sole Proprietorship) instead of Form 1040, Schedule A (PDF), Itemized Deductions. Your gains or losses, however, would be reported on Form 1040, Schedule D (PDF), Capital Gains and Losses, unless you file an election to change your method of accounting.

If your trading activity is a business and you elect to change to the mark-to-market method of accounting, you would report both your gains or losses on Part II of Form 4797 (PDF), Sales of Business Property.

The mark-to-market method of accounting cannot be revoked without the consent of the Secretary. Though there is no publication specific to day traders, information for traders in securities and commodities is in Internal Revenue Code Section 475(f) and Revenue Procedure 99-17, Revenue Procedure. 99-49, and Publication 550 (PDF), Investment Income and Expenses.

For details about not-for-profit activities, refer to Chapter 1 in Publication 535 (PDF), Business Expenses. That chapter explains how to determine whether your activity is carried on to make a profit and how to figure the amount of loss you can deduct.

Regardless of whether your day trading activities are reported on Schedule D or on Form 4797, you may need to pay tax on your gains by following the requirements for making estimated tax payments on Form 1040ES (PDF), Estimated Tax for Individuals.

References:

  • Publication 535 (PDF), Business Expenses
  • Publication 550 (PDF), Investment Income and Expenses
  • Form 3115 (PDF), Application for Change in Accounting Method
  • Form 4797 (PDF), Sales of Business Property
  • Form 1040ES (PDF), Estimated Tax for Individuals
  • Internal Revenue Code Section 475(f)
  • Revenue Procedure 99-17

10.3 Captial Gains, Losses/Sale of Home: Mutual Funds (Costs, Distributions, etc.)
If I sell one mutual fund and use the proceeds to buy another, do I have to report the capital gains or can I wait until I sell and don't buy another fund? Does it matter if I stay within the same family of funds?

You would have to report any capital gains realized on the sale. Even assuming this transaction meets the requirements of an exchange, rather than a sale, the exchange of shares of one fund for those of another is a taxable exchange. This is true even if both funds are within the same family of funds.

References:

If my children have mutual funds, how are the dividends and capital gains reported?

If a child is 14 years old or older and has a requirement to file an income tax return, he or she would report dividends and capital gains no differently than any other taxpayer. If the child is under age 14 and his or her only income is from interest and dividends (including capital gain distributions), the child's parents can make an election to include the income on the parent's return. If the parents make this election, then the child does not have to file a return. The election is made on Form 8814 (PDF), Parent's Election To Report Child's Interest and Dividends.

In order to make the election under Form 8814,

  • the child must be required to file a return,
  • the dividend and interest income cannot exceed $7,500
  • there must be no estimated tax payment made for the year and no prior overpayment applied to the tax year under the child's name and social security number,
  • there must be no federal tax taken out of the child's income under the backup withholding rules, and
  • the parent must be the parent whose return is used for the special tax rules for children under 14.

If a child under the age of 14 has investment income and the parents do not make the above election, the child reports the income as any other taxpayer would. Special rules on how the investment income is taxed, however, may apply. A child under the age of 14 with investment income (interest, dividends, capital gains, etc.) of more than $1,500 may be subject to the parents' tax rate. The special tax computation is figured on Form 8615 (PDF), Tax for Children Under Age 14 Who Have Investment Income of More Than $1,500.

For more information, refer to Publication 929 (PDF), Tax Rules for Children and Dependents

References:

  • Form 8814 (PDF), Parent's Election To Report Child's Interest and Dividends
  • Form 8615 (PDF), Tax for Children Under Age 14 Who Have Investment Income of More Than $1,400
  • Publication 929 (PDF), Tax Rules for Children and Dependents

I have both purchased and sold shares in a money-market mutual fund. The fund is managed so the share price is constant. All gain is reported as dividends. Do I have to report the sale of these shares?

Yes, you report the sale of your shares on Form 1040, Schedule D (PDF), Capital Gains and Losses. Generally, whenever you sell, exchange, or otherwise dispose of a capital asset, you report it on Schedule D.

If the share price were constant, you would have neither a gain nor a loss when you sell shares because you are selling the shares for the same price you purchased them.

If you actually owned shares that were later sold, the fund or the broker should have issued a Form 1099-B There is no requirement with that form that there be gain or loss on the sale, only a sale or exchange of an investment asset and sales proceeds.

References:

If I previously sold shares of a mutual fund and reported the gains or losses using the FIFO method, can I switch to an average basis method?

Yes, you can. The only requirement for using an average basis is that you acquired the shares at various times and prices, and you left the shares on deposit in an account handled by a custodian or agent who acquires or redeems those shares. An average basis method, once adopted, must be disclosed on your tax return and the method cannot be changed back without permission from the Commissioner of the Internal Revenue Service.

Before computing the basis of shares sold using an average basis, ensure that you have reduced your previous total basis by the cost of the shares accounted for using the FIFO method.

References:

How do I tell the IRS I used an average basis method in reporting the gain or loss from my mutual funds?

Either write the name of the average basis method used as a notation on Form 1040, Schedule D (PDF), Capital Gains and Losses, or attach a sheet to the Schedule D showing in detail how you computed the basis of the shares sold. Whenever you attach a statement to your return, include your name(s) and social security number(s).

References:

I received a 1099-DIV showing a capital gain. Why do I have to report capital gains from my mutual funds if I never sold any shares?

A mutual fund is a regulated investment company that pools funds of investors allowing them to take advantage of a diversity of investments and professional asset management. You own shares in the fund, but the fund owns assets such as shares of stock, corporate bonds, government obligations, etc. One of the ways the fund makes money for its investors is to sell these assets at a gain. When this happens, the nature of the income is capital gain, which gets passed on to you. These are called capital gain distributions, which are distinguished on Form 1099-DIV from income that is from other profits, called ordinary dividends.

References:

Where are mutual fund short-term capital gain distributions reported?

Capital gain distributions from a mutual fund are by definition long-term. That's why they appear only in Part II of Form 1040, Schedule D (PDF), Capital Gains and Losses. The annual statement you receive from your mutual fund may list short-term capital gains, but your Form 1099-DIV will show those amounts as ordinary dividends.

Ordinary dividends (which include the mutual fund's profits from short term capital gains) are reported on Form 1040, Schedule B (PDF), Interest & Dividend Income, or Form 1040A, Schedule 1 (PDF), Interest and Ordinary Dividends, if the total is over $400. In addition, you enter the total ordinary dividends on line 9 of Form 1040 or line 9 of Form 1040A.

Refer to the line 13 instructions of Form 1040 for exceptions when you can enter capital gain distributions directly on line 13 of Form 1040 without having to file Schedule D.

References:

My end-of-year statement from a mutual fund company showed amounts in 3 categories: (1) capital gains, (2) short-term capital gains, and (3) ordinary dividends. When my Form 1099-DIV came, the short-term capital gains were lumped in with ordinary dividends. Which is correct and where do I list the short-term capital gains?

Your Form 1099-DIV is correct, but so is your annual statement. For the purpose of reporting taxable income on your tax return, capital gain distributions are defined as long-term capital gains only. Short-term capital gains are taxed as ordinary income and are therefore treated as ordinary dividends on Form 1099-DIV.

Report the fund's short-term capital gains as part of your total ordinary dividends on line 9 of your Form 1040 or 1040A. (You may have to also report them on Form 1040, Schedule B (PDF), Interest & Dividend Income or Form 1040A, Schedule 1 (PDF), Interest and Ordinary Dividends. Refer to the instructions to the schedule.)

References:

How can I use mutual fund short-term capital gains, which are reported on Form 1099-DIV in Box 1 as "Ordinary Dividends," to help offset short-term capital losses?

You cannot. You did not sell the assets that produced this income, the mutual fund did. All income that is taxed as ordinary income flows through to you as ordinary dividends, whether the income is from interest, dividends, or the sales of short-term capital assets.

In the same manner, you report capital gain distributions as long-term capital gains on your return regardless of how long you have owned the shares in the mutual fund. This is because the asset was held and then sold by, the mutual fund, not by you.

Report your total ordinary dividends (including the short-term capital gains in your mutual fund) on Form 1040, line 9, or Form 1040A, line 9, with your other dividends, if any. You may also have to file Form 1040, Schedule B (PDF) , Interest & Dividend Income or Form 1040A, Schedule 1 (PDF), Interest and Ordinary Dividends.

References:

How do you list gains from mutual funds on Schedule D and Form 1040 when some mutual funds list short-term capital gains separately and others lump short-term capital gains and taxable dividends together as dividends?

Only the capital gain distributions are reported on Form 1040, Schedule D (PDF), Capital Gains and Losses. They are reported in Part II as long-term capital gains. Short-term capital gains are taxed as ordinary income and are therefore treated as ordinary dividends on Form 1099-DIV. They are reported on line 9 of Form 1040 (PDF) or Form 1040A (PDF).

Because many mutual fund companies send out annual fund statements as well as Forms 1099-DIV, or "consolidated statements," some confusion has arisen regarding short-term capital gains. The purpose of Form 1099-DIV is to provide you with information to report income correctly on your tax return.

The annual report often breaks down the income from fund activity as dividends, tax-exempt dividends, short-term capital gains, long-term capital gains, returns of capital, and undistributed capital gains. Form 1099-DIV, on the other hand, will show only ordinary dividends (which includes the fund's short-term capital gains), capital gain distributions, and returns of capital (nontaxable distributions).

Mutual fund companies may combine the annual fund information with the Form 1099-DIV information into a consolidated statement. If this is what you receive, look for the part of the statement identified as the Form 1099-DIV or that contains language such as "in lieu of Form 1099-DIV."

References:

If a mutual fund's assets earned tax-free dividends, are capital gains tax free when the fund is sold?

No. The kind of income the assets in the fund earn is tax-free. When you sell your shares in the fund, a taxable gain or deductible loss is realized on the sale. This is the true also for the sale of tax-exempt securities such as municipal bonds.

References:

On December 20, I received a large mutual fund distribution. Due to the large distribution I'm going to owe $7000 when I file my return. Is it okay to just pay the $7000 when I file my return?

If the $7,000 in tax is a result of a distribution not covered by prepayments of tax, either through income tax withholding or estimated tax payments, you should make an estimated tax payment by January 15th of the next year. If you wait to pay the $7,000 with your return, you may be penalized for an underpayment of estimated taxes. Even if you make an adequate payment of tax by January 15th, you may be assessed an estimated tax penalty by the IRS service center when your return is processed. This is because estimated tax payments are normally made in four equal installments and the IRS will not know your liability occurred in the fourth quarter unless you file Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts.

You may be subject to the penalty if you owe at least $1,000 in tax after subtracting your withholding from your estimated tax liability, and you did not prepay at least 90% of your current year's tax or an amount equal to 100% of your previous year's tax. (The latter percentage is higher for higher-income taxpayers with adjusted gross incomes from the previous year of more than $150,000.)

If you make an adequate payment by January 15th but made no earlier estimated tax payments, use Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts, to compute your penalty. Check the box on the front page selecting the Annualized Income Installment method, and then complete Schedule AI on page 3. When you compute the penalty on page 2 of that form using the numbers from Schedule AI, your penalty will be $0. Even if you did not make the January 15th payment, the annualized income method on Form 2210 may significantly reduce the estimated tax penalty if the income for which there was no prepayment of tax was earned in the third or fourth quarters of the year.

For more information on estimated tax payments and the underpayment of estimated tax penalty, refer to Publication 505 (PDF), Tax Withholding and Estimated Tax.

References:

  • Publication 505 (PDF), Tax Withholding and Estimated Tax
  • Form 2210 (PDF), Underpayment of Estimated Tax by Individuals, Estates and Trusts

11.4 Sale or Trade of Business, Depreciation, Rentals: Sales, Trades, Exchanges
Can you sell rental property and reinvest it into rental property without paying capital gains tax?

No. However, rental property may be exchanged directly for other rental property of like kind. Gain realized from such an exchange is deferred. For additional information on like-kind exchanges, refer to Publication 544 (PDF), Sales and Other Dispositions of Assets.

References:

I have heard that I can sell my rental property and use the proceeds to purchase rental property of equal or greater value and the transaction is viewed just like an exchange in that the tax is deferred until the new property is sold. Is this true?

What you have heard about is a like-kind exchange. A like-kind exchange, when properly executed, represents a way to postpone the recognition (taxation) of gain essentially by shifting the basis of old property to new property, equal to the amount of the postponed gain. There are several rules and restrictions that must be strictly adhered to in order for a successful exchange to take place. For more information refer to Publication 544 (PDF), Sales and Other Disposition of Assets, and Form 8824 (PDF) Instructions, Like-Kind Exchanges.

References:

We sold a rental property last year and used the 1031 Tax Deferred Exchange law to defer the gain into another like-kind property. How do I report this transaction on my tax return?

Report the exchange of like-kind property on Form 8824 (PDF), Like-Kind Exchanges. The instructions for the form explain how to report the details of the exchange. Report the exchange even though no gain or loss is recognized.

If you have any taxable gain, resulting from the transaction, because you had a partially deferred exchange or otherwise received money or unlike property, report it on Form 4797 (PDF), Sale of Business Property, and Form 1040, Schedule D (PDF), Capital Gains and Losses. Refer to Publication 544 (PDF), Sales and Other Dispositions of Assets, which has a detailed section on qualifying like-kind exchanges.

References:

Can we move into our rental property, live there as our main home for two years, and sell it without having to pay capital gains tax?

You may be able to exclude your gain from the sale of your main home that you have also used for business or to produce rental income if you meet the ownership and use tests, detailed in Publication 523 (PDF), Sale of Your Home.

However, if you were entitled to take depreciation deductions because you used your home for business purposes or as rental property, you cannot exclude the part of your gain equal to any depreciation allowed or allowable as a deduction for periods after May 6, 1997. (Note: If you can show by adequate records or other evidence that the depreciation deduction allowed (did deduct) was less than the amount allowable (could have deducted), the amount you cannot exclude is the smaller of those two figures.)

The gain, exclusion, and depreciation recapture should be reported on Form 1040, Schedule D (PDF), Capital Gains and Losses, as described in Publication 523 (PDF), Selling Your Home.

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12.8 Small Business/Self-Employed/Other Business: Schedule C & Schedule SE
I buy and sell stocks as a day trader using an online brokerage firm. Can I treat this as a business and report my gains and losses on Schedule C?

A business is generally an activity carried on for a livelihood or in good faith to make a profit. Rather than defined in the tax code, exactly what activities are considered business activities has long been the subject of court cases. The facts and circumstances of each case determine whether or not an activity is a trade or business. Basically, if your day trading activity goal is to profit from short-term swings in the market rather than from long-term capital appreciation of assets, if your income is primarily from the sale of securities rather than from dividends and interest paid on securities, and if you expect this income to be your primary income for meeting your personal living expenses, i.e. you do not have another regular job, then your trading activity might be a business.

For details about not-for-profit activities, refer to Publication 535 (PDF), Business Expenses. That chapter explains how to determine whether your activity is carried on to make a profit and how to figure the amount of loss you can deduct.

If your trading activity is a business, your trading expenses would be reported on Form 1040, Schedule C (PDF), Profit or Loss from Business (Sole Proprietorship), instead of Form 1040, Schedule A (PDF), Itemized Deductions. Your gains or losses, however, would be reported on Form 1040, Schedule D (PDF), Capital Gains and Losses, unless you file an election to change you method of accounting.

If your trading activity is a business and you elect to change to the mark-to-market method of accounting, you would report both your gains or losses and your trading expenses in Part II of Form 4797, Sale of Business Property. See Publication 550 (PDF), Investment Income and Expenses, for details.

A change in your method of accounting requires the consent of the Commissioner and can not be revoked without the consent of the Secretary. Though there is no publication specific to day traders, the details for traders in securities and commodities are covered in Internal Revenue Code Section 475(f) and Revenue Procedure 99-17.

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12.9 Small Business/Self-Employed/Other Business: Starting or Ending a Business
How is the withdrawal of a partner handled?

Unfortunately, the answer to this question has many variables. Publication 541 (PDF), on Partnerships should provide the information needed.

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13.4 Aliens and U.S. Citizens Living Abroad: Nonresident Alien - General
I am a nonresident alien and invested money in U. S. stock market through a U.S. brokerage company. Are the dividend and the capital gains taxable? If yes, how are they taxed?

Generally, capital gains received by a nonresident alien not present in the United States for 183 days or more are not taxable in the United States. Certain gains, however, are subject to the 30% withholding rate or if applicable, a reduced tax treaty rate on the gross amount of the following items:

  • Gains on disposal of timber, coal, or domestic iron ore with a retained economic interest, unless an election is made to treat those gains as income effectively connected with a U.S. trade or business,
  • Gains on contingent payments received from the sale or exchange after October 4, 1966, of patents, copyrights, secret processes and formulas, goodwill, trade marks, trade brands, franchises, and other sale property,
  • Gains on certain transfers of all substantial rights to, or an undivided interest in, patents if the transfers were made before October 5, 1966, and
  • Certain gains from the sale or exchange of original issue discount obligations issued after March 31, 1972.

Dividends are withheld upon at the 30% or lower tax treaty rate. If your withholding is not at the correct rate, a nonresident alien should file Form 1040NR (PDF), U.S. Nonresident Alien Income tax return to claim a refund of withheld taxes.

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