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When I go through the bank statement I print copies of any checks I might need as proof. It's a nuisance, but there are few, and it will save me trouble if I ever need them.

I hadn't thought about this - can you give a couple of examples of stuff to keep ?

Anything that might be needed to support a future tax return... such as payments to doctors, pharmacies, etc.; charitable contributions; contributions to IRA accounts; education expenses; investment expenses; tax preparation fees; real estate tax payments (if not paid through escrow); other deductible employee/business expenses; estimated tax payments; etc.

Don't forget to make copies of any checks that pay for capital improvements to your house. These will add to your cost basis. Even though there is currently a tax exemption on the first $250K/$500K of gain when you sell your primary residence (subject to certain qualifications), there is no guarantee that the rules won't change, or that your eventual gain won't exceed the exclusion limits. When you sell your house years from now, it will be very difficult to go back and find these checks if you don't start a permanent file for them today.


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