https://taxfoundation.org/blog/how-many-words-are-tax-code/
A typical federal tax filing for our household is over 100 pages long, and that’s just the stuff that we need to mail. The accompanying directions and worksheets are probably close to 1000 pages.
Also, lots of the directions are incredibly obfuscated once you start getting into those 1000 pages.
> If you do A and not B then you can do C.
> Example calculation of C (usually over a page long):
> Bob wants to do C but encountered corner case exceptions E and F in the absence of event G. That implies B, so here’s the arithmetic for doing D (which is covered elsewhere in this book, and is probably irrelevant to your situation).
This is just standard stuff TurboTax handles. God help people with filings too complicated for that!
(And, yes, I used to do taxes by hand.)
One year, I had to spend a good deal of time working around a cycle in my taxes--VA wanted me to do my CA taxes first and CA wanted me to do my VA taxes first, and the instructions that explained how to handle this situation were only one on the one form that needed to be used to solve it, with nothing telling you maybe you should look for that form instead.
Furthermore, there's quite a few cases where the instructions basically tell you "fill in the number that belongs here" without giving a good idea of what numbers actually belong there. Here is an example of such an instruction in its entirety:
> Enter in line 5 the amount of pension, annuities, IRA/Keogh distributions not taxed on your Massachusetts Form 1.
The hard part of taxes isn't knowing whether or not to add or subtract two lines. It's knowing which lines shouldn't be 0!
Whether or not you do your taxes by hand, you should probably have a good idea of your income sources.
The solution to this of course is to simplify the tax code so that you don't have so many colors to your money. I very much would love to see this happen, but it will produce howls of protests from every special interest group who benefits from special tax advantage to their interests.