Well, so far, I've been doing my own taxes for the last couple years, including 7 or 8 states a year between all the jobs.....I'm actually wondering if and when I'll get audited, but at least I'm keeping damn good records of how I figured it all out.
I'm not going to comment on the "right way" to do the taxes themselves, but as for organizing.........I use Quicken, and create my own categories for things like tickets to shows (research), black clothing (uniform), office supplies, run gear (flashlights, etc). And in addition to bank accounts and credit cards, I've set up an account I call "Out of Pocket" and that's where I put all those things I paid for in cash. And every couple ATM withdrawals or so I actually list as a "transfer" from the checking account to the "out of pocket account" to make it all work out even on Quicken. And I staple all my receipts to 3-ring notebook paper so if I need to look them up I can. I also have all my credit card statements in the back, with the non-tax related receipts stapled there for my personal use. I also put a big list in the front of the notebook for major purchases of the year, both theatre-related and not, so I can relatively quickly find things.
Erin