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I have two DATEK accounts. The first, an IRA buy and hold RP4. The second, a play account for my day/week trades,
very short term. Q1. Do I need to enter each buy and sell on my 1999 tax form? Q2. I there an easy way to do this?


You don't need to report trades in your IRA.

Yes, you do need to report each sell in your taxable play account. But you don't report the buys until they are sold. Sales are reported on Schedule D. If your sales won't fit on Schedule D, you go to the continuation sheet, Schedule D-1. Use as many D-1s as you need to report everything. Using a computer tax prep progam may make it easier as it should calculate the gains/losses on each sale and the totals for you.

Datek should send you a list of your sales in January, including date sold and sales price. They also will send this info to the IRS. You need to keep track of your buys. You will get your date acquired and cost from your trade confirmations or monthly statements.
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