I have no clue what this 1099 form is even asking for because it's so broken and they (apparently) removed any form of tech support chats

It is asking for the cost or adjusted basis.  That would be the amount you paid for it.  

but paid for which one is my question. It's got like my whole trading history in there but it's all overlapping and there's nothing highlighted at all

I assume that the issue is with the investment that is displayed on the screen.

 

 

In TurboTax Premier Online, follow these steps.

 

1. Down the left side of the screen, click Federal.
2. Down the left side of the screen, click Wages & Income.
3. Click the down arrow to the right of Investments and Savings.
4. Click to the right of Stocks, Cryptocurrency, Mutual Funds, Bonds, Other (1099-B).
5. Click the down arrow to the right.
6. Click Edit to review/edit/correct the transaction.

It wasn't that one. As far as I can tell it was one that was part of a automatic reinvestment for $0.94 that wasn't even shown on that screen (and I had to just close out of it and go all the way back to when you input the files to fix it). Still very disappointed that there's literally no "help" option other than "pay someone to do it for you" when the input is that broken. What that screenshot doesn't show is that when you scroll it the actual checkboxes and input boxes all moved, but the background and plane text didn't scroll at all