If there's one image I had of tax preparation before I actually started preparing taxes, it was sorting through a loose pile of poorly-organized receipts, trying to categorize expenses. To my relief, this usually isn't the case.
It might be more common in coming years, when the expanded standard deduction expires and miscellaneous deductions...un-expire with it, but in the years I've been preparing taxes, this has only been a thing for self-employed people—and even then, only a minority. Most self-employed people are pretty good about keeping track of that sort of thing.
But a few clients...aren't. Maybe they're new to running a business, maybe they don't have the time to keep a proper business checkbook or spreadsheet, maybe they're just disorganized. And it can be annoying, but there's a pretty simple solution to it. Go through the receipts or whatever, put down the relevant information in a spreadsheet, then have the spreadsheet total everything and put it on the return. Thank Turing I don't have to do this junk by hand!
There are sometimes causes for irritation, like when different records list some of the same expenses and I have to make sure I'm counting every expense exactly once. But I don't mind that much. At least it's not a 1099-B.
If you sell financial securities (e.g. stocks), you'll probably get a Form 1099-B. The thing about Form 1099-B is that every individual stock transaction has to be recorded separately on your tax return. The stock sales are listed alongside sales of any other capital assets, not all of which come with fancy forms sent to the seller and IRS.
It gets worse. See, the IRS doesn't deal with cents (for reasons nobody has ever explained to me), so the basis and selling price of those stock transactions need to be rounded to the nearest dollar before I input them. But the 1099-B, in the name of accuracy, doesn't do this. The program I use provides helpful totals for short-term/long-term basis and sale prices, as does the 1099-B...but, of course, the 1099-B's values aren't rounded.
So when I finish inputting the 1099-B, I often find that the totals I input don't match the total on the form. Which means that, after inputting dozens or hundreds of individual transactions, I need to review all of those transactions to make sure I didn't miss or mistype any of them.
Schedule C expenses can be a pain, but they're usually at least a little interesting, not just copying numbers. And when you fill out Schedule C numbers, you're looking at someone trying to make a living without a corporation taking the lion's share of the value they produce. A 1099-B is practically the opposite, someone trying to gain wealth solely through their pre-existing wealth. If I'm gonna spend an hour and a half typing numbers, my sentiment towards those numbers makes a big difference on my mood.
