I just finished my taxes and filing taxes in the US is such a stshow. But where do we start? We want to simplify filing, but that might depend on simplifying the tax code, which might be orders of magnitude more difficult. Sigh!

I think opening the article this way is misleading, although they explain it better later on. This isn't about filing for free, it's about guided tax preparation. Those automated systems that ask a series of simple questions and magically submit your tax return.

That's why tax complexity is the underlying issue. To do your taxes you "just" have to follow along a 100+ page instruction booklet (plus instruction booklets for any additional forms). Even with the Free Fillable Forms (free government electronic filing for everyone with digital forms and some automated calculations) it's a pain in the butt. By rephrasing the questions, automating the calculations, and checking for errors, fairly complex taxes can be done in under an hour.

So we're playing this stupid game where the government spends the time and money to write complex taxes and all the forms and instructions to go with them, just for us to pay businesses to simplify it all so we can tell the government what our taxes really are. I hope this change takes a big chunk out of the $14 billion tax prep industry (that's more than the IRS's expenditures), because maybe when they're out of the game Congress will be a little more motivated.

The first one was an oaf in Los Angeles that charged me $500 to redo a back-of-the-envelope calculation I had already done.

The second one was an older lady in Silicon Valley. You would think she would have known how ISOs work, but she messed up the calculations anyway. There were no penalties, but she felt bad enough that she filed my taxes for free. She got cancer and retired 6 months later.

The third was a friend that prepares taxes for billionaires. His retainer is something like $15K per year. His software's calculations disagreed with my homemade spreadsheet by $40K. In April my spreadsheet ended up within a few thousand of TurboTax. He's still kicking himself over that...

Yes, the IRS could do even this for you, but there's a myth that US taxes are always monstrously complicated that everyone likes to perpetuate:

1) The tax companies like it because it keeps people scared of doing it themselves

2) Tax reform advocates like it because it's they can cluck and shake their head at the corrupt government and tax companies

3) It _can_ get complicated if you have a complicated tax situation

That's a decently idealistic viewpoint, but "complicated" doesn't necessarily mean "broken". For example, pretty much all Unix-style operating systems have not only a ton of now-unnecessary code to handle text I/O from 1960's teletype machines, but they even come with a "terminal emulator" that literally emulates the behavior of a 1960's teletype machine. That's how the command line works. You would never design it that way from the start, it's complicated, it's crufty, and it's vaguely horrifying, and yet it works and solves virtually all of the real problems that real people would have with that system. Just like letting the IRS fill out the first draft of your tax return.

Because of my immigration status I paid an accountant to prepare my forms and was a little surprised to find out I owed the IRS. I tried to work backwards to figure out why but this was all but impossible. Few of the values are labelled and all are interdependent on each other. To figure out what a single value I had to work backwards through multiple branches until I reached the root input.

I'm convinced the forms were designed by writing someone in the IRS taking the code for their tax calculators, removing the identifiers and converting it into English text. I have no idea what each variable represents so am unable to be sure the totals are correct. I got the impression that an error early in the process could easily carry through without me noticing. The whole process is opaque and doesn't make me feel like I can trust the IRS or the process to produce an accurate result.

By contrast the Australian eTax application asks me a series of yes/no questions, used that to calculate my deductions and income and showed breakdowns for each. For anything non-standard they ask you to use online calculators and provide or retain your documentation. The UK system was even easier and seemed to be calculated based on data supplied directly by employers. My wife was able to get a tax return without submitting any paperwork (there may have been a single form, I can't really remember).

There's nothing hard about updating a few values with these then you're done in five minutes. State governments already do simple walkthrough forms and federal is really no different. If you have a complex tax situation then that's your problem to deal with. Don't burden 99.9% of the population with something that should be free, should be simple, and should be fast.

As a lawyer and tax accountant, do you see a flaw in the professor's approach? Any domain expert insight here?

I do my taxes every year, sometimes long-form, sometimes with software like TurboTax. The complexity of my taxes is entirely the fault of the way in which I am required to provide information to the IRS, most of which they already know, even though I take the standard deduction and don't do any "tricks". A simply example is if you have any sort of stocks/bonds or other tradeable asset holdings. Reporting this is a massive pain in the ass, because despite the fact that Schwab/Etrade/et-al already report this to the IRS, they make you list the cost basis, date of purchase, and sale price of every transaction that occurred within the tax year as part of calculating whether or not you're eligible for long-term capital gains or are taxed at your marginal income tax rate (short term capital gains). Very closely related is transactions dealing with RSUs, which every tech worker (most of HN) has to deal with. This is despite the fact I work a relatively normal white collar job on a W-2 and don't even file a base 1099 on a yearly basis.

Taxes are complicated in the US because our tax code is bonkers and we're forced to precisely input a whole lot of spreadsheet bullshit that the IRS already knows so they can auto-check our work against their database rather than just telling me I owe them an extra $2k because despite having maximum withholding, the government wants to fuck me a little deeper in the ass. Exactly none of this is optional, I am /obligated/ to report all of this complexity, whether I paid enough or not, or I am legally penalized.

Taxes /could/ be simple, but they are not, for anyone who makes more than about $60k/yr, which is nearly half the country.

> You can dumbly supply a small amount of information and be in complete compliance with the law.

This is not only factually untrue, anyone who follows this advice is putting themselves in significant legal jeopardy.

If you chase up the comment chain you replied to, you're really agreeing with me using a tone of disagreement. sockaddr says that filing has to be complex because tax codes are complex. We both disagree with that.