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by kaffeinecoma 3717 days ago
I dread tax time every year. I'm self-employed, so I don't exactly expect it to be easy, but I generally end up spending 3-4 full days working on my return. Not including the meticulous record keeping I amortize over the year with a simple spreadsheet.

Every time I think I've finally got it figured out, there's always some weird new situation that throws a wrench in things. Common things like buying/selling a house, moving to a new state or locality, death of a parent, etc. I honestly don't know how most people ever manage to do it correctly, much less optimally.

This year it was 2 different banks that got IRA reporting wrong. Last year, Turbotax "interview mode" would not let me enter some crucial figure correctly. Previous year it was clients not sending 1099s (and agonizing over whether to just report manually or wait for the form). Two years before that it was a RITA (local tax authority) screwup.

I tried hiring a local CPA to take away some of the pain, but he ended up making a $5K mistake, and it took hours of my time to correct. I've had a good accountant in the past, so I know they can make a huge difference, but they are very hard to find.