I don't have a problem with filling out the forms by hand. The problem is that you need to know *how* to fill them out, which in the past, when I had to fill them out by hand, took hours of reading IRS publications. If you just worked at a job, didn't own anything, and had no deductible expense, not a problem. But if you own anything, whether stocks, bonds, house, or even a car, or give things to charity, lotsa luck reading all those publications. Or, if you moved for your job, or had expenses related to your job. Or had a side gig. Or any number of other things where it's not obvious how to handle them for taxes.
That's really entirely the fault of laziness by the IRS and/or Congress. We should have laws requiring all of those companies to provide the complete set of information necessary to file your taxes in a computer-digestible form. There's no excuse for having to manually change several *hundred* lines one at a time to tell TurboTax that they are short-term or long-term gains, or whatever the one random piece of information that it needs from my Edward Jones statement every f**king year on a third of the transactions because it is trying to parse a d**n PDF file.
What makes it a nightmare is that even though all of the forms theoretically have compatible fields, they aren't actually standardized in their formatting, layout, which fields are omitted, etc., and that's true even for the easy stuff like 1099-INT, much less nightmares like 1099-B. And they are provided in formats that are intended for human consumption, not software consumption, so they're having to do crazy amounts of interpretation to figure out what the numbers mean and how to correlate them with other things on a page. This is the stuff of nightmares.
Instead, these data formats should be standardized with a mandatory standard format (XML, JSON, etc.) and shared schema. Providing data in that format should be a hard requirement for all financial institutions, and if a financial institution's data is unparseable by standard tools or is wrong in any meaningful way, the company that provided it should be on the hook for the cost of any additional interest and penalties caused by the taxpayer relying on that data blob.
Once you have that sort of strict data portability and interpretability codified into your tax code, tax filing software *should* become easy, because it's just shuttling data from one strict standard format into another strict standard format. This would be very easy for the financial institutions to do, because they already have the data. It's hell on earth for TurboTax to "Intuit" from human-readable PDF files. (See what I did there?)
