No. of Recommendations: 2
Once I'm retired and cruising around the world in my boat, do I really need to keep a file drawer of every single stock purchase I've ever made?

Yes, until you sell.

Are the online brokers helpful in calculating your tax basis?

Don't count on it. Even assuming they today can cough up everything you need, they don't have to. Witness Verizon DSL, which used to provide really good tech support but has now moved it offshore, inducing a 4-day nightmare for me the last time I had a problem. I digress.

With individual stocks there is no substitute for purchase confirmations, with appropriate notations for basis adjustments from splits/mergers/spinoffs that happen while you hold the stock.

You have more leeway with mutual funds because you can use average cost basis. If you decide to go that way, keep purchase confirmations until you get a statement (usually quarterly) showing them. Keep quarterly statements until you get an annual statement showing the year's transactions. Keep annual statements until you've sold everything for that fund.


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