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Question about the paperless society and IRS documentation requirement: I know I must keep all my stock and mutual fund documentation forever. Now, I'm getting them, not a physical paper, but emails, leading to PDFs on various websites. 1) is this trustworthy? 2) sane? and 3) what might the options be, aside from printing everything up every month?

You don't have to keep all the documentation forever, you just have to keep track of the relevant documentation.

In most cases, the 1099s have all the relevant data. I maintain an annual spreadsheet to cover stock/ETF transactions with columns similar to the Schedule D, plus a couple of additional columns. One additional column is for keeping track of partial share sales i.e. If I buy 200 shares at time X, sell only 100 shares at time Y, that row gets a P or a check in its respective cell to denote a partial sell. The second additional column is for special cases e.g. wash sales, RoC (Return of Capital), etc. The spreadsheet can validate the 1099, or vice versa. Lot of work? Not really, perhaps an hour or so a month that pays off huge during tax filing time.

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