Retirement tax questions

First, I would round all the transactions to the nearest dollar.

IRS Publication 17, page 14 states:

Rounding off dollars

You can round off cents to whole dollars on your return and schedules. If you do round to whole dollars, you must round all amounts.

Make sure to retain paperwork should a tax authority contact you at a later time.

If you were to group your personal sales, there would be as many as four categories:

• Personal item for loss reports $0 gain/loss,
• Personal item gain long-term basis,
• Personal item gain short-term basis, and
• Personal item, no gain or loss.

Here are examples.

                       Selling           Cost

                       Price              Basis

T1                   $500              $1,000        Capital loss on personal item = $0 gain/loss

T2                   $400               $300          LT Capital gain on personal item = $100 gain

T3                   $0                   $0               ST Capital gain on personal item = $0 gain/loss

T4                   $100               $100          No capital gain or loss              = $0 gain/loss

                        $1,000           $1,400

In TurboTax Premium Only, report Personal item sales by following these directions.

• Down the left side of the screen, click Federal.
• Down the left side of the screen, click Wages & Income.
• Click on the down arrow to the right of Other Common Income.
• Click to the right of Form 1099-K.
• At the screen Did you get a 1099-K?, select Yes.
• At the screen How would you like to upload your 1099-K? click Type it in myself. 
• At the screen Which type of income is your 1099-K for, select the button for Personal item sales.  Click Continue.
• At the screen Let's get the info from your 1099-K, enter the information.  
• Box 1a is $1,000 but items T1 and T4 total $600 and report $0 gain.    
• Click Continue.
• At the screen Personal Item Sales, because $600 of the selling price will not be reported, enter $600 under I sold some items at a loss or had no gain. 
• Learn More provides detailed information for the next steps.  Click Continue.
• At the screen Your 1099-K summary, notice that the income relates to ‘Personal Items’.  Click Done.
• At the screen Your income and expenses, scroll down to Investments and Savings (1099-B, 1099-K….).  Click to the right.
• At this screen, you will be asked to Review the Personal item sales (1099-K).  Select Review.
• At the screen Now, enter one sale…., answer questions about the personal item sale.  
• Because you are only reporting the gain transaction, report $400 as Proceeds and $300 as Total amount paid.
• Click Continue.
• At the screen, Let us know if any of these situations apply to this sale, sales expenses may be recorded.

The entry will be reported:

• on Schedule D of the Federal 1040 tax return, and 
• on line 7 of the Federal 1040 tax return.