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by mountainofdeath 1129 days ago
It's probably more-so that above a certain income threshold, your tax return becomes exponentially more complex.

Free-file is useful when all you have is 1-2 above-board wage earning jobs, maybe with a 1099 contract job where the employer is nice nice enough to pre-fill the form out for you.

Once you start dealing with non-trivial amounts of dividends, interest, securities, partnerships, real-estate, you really do need a professional to keep things organized.

3 comments

I get that, but why use income as a proxy for complex tax items? A W2 that takes home 400k using standard deduction for example is easier than someone self employed with several deductions that makes 100k.
> above a certain income threshold, your tax return becomes exponentially more complex

For some people. A person working a single job as a programmer earning $300k in straight W-2 income (no RSUs, etc.) does not have more complex taxes than a person earning $100k from a combination of their podcast + a few rental properties. There's no logic to means-testing this kind of service, where there would be for feature-testing (i.e. "Does all your income come from your job?").

RSUs don't really complicate anything, they are straight W-2 income.
If you sell them it gets more complicated because your broker is for some reason forbidden from reporting the correct cost basis even though they know it.
I make a lot more than that, but as long as I remain a simple W2 earner it is still ridiculously easy to file taxes and I shouldn't be charged extra for it.