Another reason to stick to simple index funds, and if you want to play stocks do it in a tax privileged account so you don’t have to bother with the paperwork.

I learned that the hard way.

A few non-IRA investments become very annoying to file after a couple years.

The current tax system is absolute garbage.

This has always been my excuse for not trying FreeTaxUSA. I figured it was only for people who have extremely simple 1040 returns + a few stocks or interest. My federal return is 20 pages long, including schedules 2, 3, B, D, Form 8606's, 8889 and on and on and on. I've always been afraid I'll get 85% through and realize I need a more expensive tax prep software to file everything I need to file--and then have to go back to TaxAct and re-type everything anyway.

You just input summaries (like two per broker max) and then mail in your 1099 or w/e to the IRS. Doesn't take that long at all