I think "gnarly" would be an exaggeration, but it all adds up to being just complicated enough to be a bit of a pain. I have: I have: * A job with a W-2 * 2x

I think "gnarly" would be an exaggeration, but it all adds up to being just complicated enough to be a bit of a pain. I have: I have: * A job with a W-2 * 2x brokerage accounts with 1099-INT + 1099-DIVs * An HSA with a 1099-SA / 5489-SA forms * A housing coop with a 1098 mortgage interest form, and property taxes to deduct * A mortgage with a 1098 mortgage interest form Some pain points: * TurboTax wants to know if I paid Alternative Minimum Tax in the past, but doesn't seem to check its own records (I have only ever used TurboTax), or give me an easy way to check that (i.e., go look at line / box #xx on your previous 1040s). My memory is that I did end up doing AMT one year, and I think that somehow influences future years? * I ended up doing estimated tax payments one year (TurboTax gave me the forms and details for this), but then the next year I didn't understand that I needed to deduct those payments (or rather, I had imagined TurboTax would know / ask me about that, but it didn't in any clear fashion). I got a letter from the IRS about the discrepancy, I had to send them the estimated tax payment data, they sent me an adjusted form, it was all fine in the end but it took some extra time + hassle to work through. * The brokerage accounts lead to capitals gains and losses which can need carrying over across years, and the dividend income seems to be enough to cause the estimated taxes in some years but not others. * TurboTax is just way more annoying than it needs to be with its upselling, animations, sometimes vaugely worded questions, and apparent reluctance to use last year's records. * Overall, my assets / income aren't massive or anything, but it wouldn't suprise me if someone being paid $500 / year or thereabouts could pay for themselves in saved time + mistakes or optimization suggestions.