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Greetings, Larrypie, and welcome. You asked:

<<I debated long and hard on whether to post this here or on the taxes board. Heads won.

I have deceided to retire and my final paycheck was 4/15/99 (coincidently enough :-). Here is what I have for taxable income this year:

1) Salary
2) Required Minumum Dist from a Beneficiary IRA.
3) Liquidation of a Beneficiary IRA.
4) Carryover Roth IRA conversion income.
5) Capital Gains on Stock.
6) Carryover loss from 1998 on sale of Real Estate.
7) Additional loss in 1999 on Real Estate.

I should be OK on #1. I don't know when the IRS expects #4 to occur. I was having extra withheld from #1 to cover #4. #6 & #7 (which occurred in January) should swamp #5 (November timeframe) and I will probably still have a carryover into 2000. #2 & #3 have not yet occurred.

Do I need to file Estiamted Tax Returns and when do I need to file them? I have never filed estimated taxes before, so this is kind of new to me. >>

You might. All you can do is run some projected numbers to see. Look at this year's tax return and try to project your taxable income for next year along with your estimated withholding. Account for your deductions and exemptions, look at the tax tables, and see what the bill will be. If your withholding is not enough and the shortfall doesn't exceed 10% of the amount due, or if your withholding will be at least as much as your 1998 tax, or if your total 1999 tax less withholding is less than $1K, or if you didn't owe any taxes in 1998, then you don't have to worry. Otherwise there's a penalty due, and to avoid the penalty you must make estimated tax payments.

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