I used TurboTax last year for the first time and learned you had to attach hundred of pages of your trades to your federal tax filing via postal service. TurboTax, at that time, at least told me that the number of transactions was too much and I had to do it that way. I paid at least $20 to print (most of the cost) and mail.
This year, I thought I kept that number down and it accepted my imports, but as soon as I went to file there no ZERO indication that there would be a problem filing. I paid for TurboTax online and attempted to file, but ran into a problem. A problem that 3 customer service calls could not figure out. I wonder who tests this garbo software and who trains their customer service to debug shit (because they don't).
I only figured out the problem after starting from scratch and then importing the lower than 4k trades to see the software not want to produce any printed material. Why the hell is starting from scratch made so hard to do anyway? Importing partial sections should be easy.
Anyway, Turbotax advertises 4k transaction count or whatever and the software says nothing was wrong and doesn't work. I used TaxAct to do my taxes this year. It required a bit of data parsing, cleaning and some manual entry so after a few hours I got it filed through them. They supported attaching Form 8949 attachments which meant I could split up a 200+ page pdf into smaller sizes and attach them for electronic transfer to the IRS for free. IRS clearly isn't the one behind the times with this feature. TurboTax doesn't support this feature, so it is legacy and sucks ass. The efile transfer is a bunch of PDFs anyway, so why not let people attach 8949 pdf forms. PDF parsing of IRS attachments shouldn't be a non trivial feature especially with Machine Learning and Computer Vision.
The only problem i have with TaxAct is the lack of importers. There were a few bugs I encountered such as javascript bugs during CSV import (which got fixed at some point) and the attachment page not showing the "large attachment" error. I had to open up the browser inspector when I submitted the attachment to find out it was too large. I would blame a browser extension for interrupting it, but I tried on two browsers, soo.
I filed a dispute with my credit card provider since Intuit did not want to refund me for the online version of their shit software. I couldn't file or print or do anything, so why the phuk should I pay for Federal Tax filing which couldn't happen. I and their customer service had zero idea what was going on by the time I filed it. I've been credited by my CC provider generously since I filed it. First chargeback ever. PHUK Intuit.
I learned a few new things along the way though at least. Had TurboTax worked, I would have submitted some incorrect information (TurboTax's importer isn't very good at transaction classification) and not learned anything new, so it is a kind of blessing.
I probably will be going to a CPA next year since there are business transactions this year.