Earlier quoted context omitted.
I came here to write something along these lines. For the simplest cases, filing is free and really easy now. Everyone who needs TurboTax now would need something roughly as complicated until our entire tax regime is overhauled. Adding to the types of really common situations where you do have to provide context the IRS doesn't already have: - side-hustle contracting (IRS doesn't know what expenditures are for the bu…
>- stock sales (your broker may not know your basis) This used to be a real nightmare especially when there were acquisitions in stock, splits, etc. There were a couple times over the years when I just said F' it and put down a reasonable number. But these days, unless you have some pretty old investments, the brokerages generally track your basis.
Yes, but IIRC if you transfer investments between brokers you are back to tracking basis yourself (if you're lucky, the new broker will allow you to enter the basis after the transfer).
But agree in the general case that it's not a problem for younger people. (Gen X and older may indeed have some of those pretty old investments lurking in their portfolios.)