I've filed my taxes myself for several years. A couple of times the IRS sent me letters after the fact saying I messed something up. Then it's another several hours combing through all their paperwork trying to correct whatever they said I did wrong. One time they directed me to "explain why you won't make this mistake again in the future." Which is a particularly asinine thing to ask. "Well, Mr. Tax Man Sir, I probably won't make that particular mistake again because now I know not to make that particular mistake again."

This year things got complicated enough that after spending an entire Saturday staring at forms, instructions, and spreadsheets trying to figure out what I was supposed to do, I finally gave up and hired a CPA that specializes in tax returns do my 1040.

The whole thing ended up being 27 pages long. I guess I needed forms 1040-ES, 2210, 8949, 8995-A, 8960; Schedules 2, B, D, and 8812; and several worksheets. I consider myself fairly capable and experienced in filing my own taxes having done it 20-something times, but I don't think I would have ever figured out that I'd need all those forms and schedules this time around.

It's particularly frustrating that they are somehow able to tell me that it's wrong after the fact and harass me to correct it. If they can do that, why not just tell me what they think it's supposed to be in the first place, and then give me the option of correcting what they send me if I spot something that doesn't make sense to me?