Seems like TurboTax is probably not worth the hassle of trying to use for free. They try to steer you at every turn into accidentally accepting the paid features, and if you manage to make it through the maze there doesn't really seem to be much left that makes them better than any of the simpler competitors if you stick to the free tiers - no saving your information year over year, no automatically importing the super complex statements from robo-advisors like Betterment, etc.

It also seems like most software engineers won't qualify for free file anyway, because it has an income limit of $69,000 a year as far as I can tell.

One thing I genuinely wonder, at what point will digital/web-based services become the default for handling information by the government and every other large institution? Will it ever happen in my lifetime? Why are we still having to pay for 3rd party software to fill out physical forms? Even docusign, while it has become very prevalent for most contracts these days and is very convenient, is still requiring that you fill out a scanned image of a physical piece of paper, instead of just making the contracts web-based. Why?? Why doesn't the IRS just have a web app like turbotax for everyone to file taxes through? And if the answer is that the tax code is way too complicated that it's prohibitively expensive for the government to build a site as comprehensive as Turbotax, then fix it!