Question 1 (Recommended): You should separate transactions by holding period -long term from short term. Then you can enter them yourself as two summarized sales.
- Long term is a holding period of more than one year and receives capital gain tax treatment (0%, 10%, 15%, 20% depending on your regular rate of tax)
- Short term is a holding period of one year or less and receives ordinary gain tax treatment (your regular rate)
Columns should be similar to Form 8949 (grouped together by holding period):
- Description
- Date Acquired
- Date Sold
- Proceeds
- Cost
- Gain/Loss
These worksheet can be filed after your tax return is accepted.
If you are e-filing your tax return, then mail your statements along with Form 8453 to:
Internal Revenue Service
Attn: Shipping and Receiving, 0254
Receipt and Control Branch
Austin, TX 73344-0254
If you need a blank Form 8453, you can download this pdf, enter your address information and check the box for Form 8949 (this form is really just a cover sheet).
2. My suggestion is to use the method suggested in number 1. If you have excel type sheets you can reorganize and auto calculate for your totals. This is perfectly acceptable to the IRS and it may make the tax return easier to complete.
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