That's smart, I never thought about that! How much of a difference could the car sales tax actually make though? I'm trying to decide if it's worth the trouble of finding all the paperwork from my purchase last year.

For a typical car purchase, you might be looking at hundreds or even thousands in deductible sales tax. On a $25,000 car with 7% sales tax, that's $1,750 potentially deductible. On a $40,000 car, it could be $2,800 or more depending on your state's tax rate. That's significant enough that it could tip the scales if you're close to the itemizing threshold. The documentation is pretty simple - just need your bill of sale showing the purchase price and tax paid. Most people keep this with their important car documents anyway.

So basically we're all answering a bunch of questions that probably don't matter? That's super annoying. Why can't they just ask up front if we're likely to itemize or take the standard deduction, and skip all these irrelevant questions?

Thanks, that's really helpful! Did your surgeon provide this breakdown automatically or did you have to specifically request it? And did you need any special form or just the regular itemized receipt?

You absolutely need to specifically request the breakdown - most surgeons don't automatically provide it because they're thinking about insurance coding, not tax deductions. I had to explain exactly why I needed it, and even then had to follow up multiple times. You don't need a special IRS form, but you do need a detailed invoice or letter from your surgeon that clearly separates costs between medically necessary procedures and cosmetic components. My surgeon provided an itemized receipt with each procedure component listed separately along with a letter explaining which aspects were addressing medical conditions. Keep these documents with your tax records - don't just rely on the standard receipt they give everyone.

Medical tourism can be really risky for complex procedures! My cousin had complications from her overseas tummy tuck and ended up spending way more fixing everything back in the US. Plus those expenses definitely wouldn't be tax deductible.

What if one person gets bonuses that vary year to year? That's what always throws off our withholding calculations.

For variable bonuses, I recommend using the IRS Withholding Estimator tool and updating your W-4 after any significant bonus payment. Most companies withhold bonuses at a flat 22%, which might not be enough depending on your tax bracket. Another approach is to estimate your total bonus amount for the year (maybe based on last year plus a little extra) and add additional withholding in Step 4(c) to cover the difference. Then if you get more than expected, you can submit a new W-4 to adjust. It's a bit of work, but it's better than getting hit with a big tax bill and possibly underpayment penalties.

This is the clearest explanation I've seen! One question - if my spouse doesn't work currently but might start later this year, should I still check that box in Step 2c now? Or wait until they actually get a job?

Do you know if Cash App Taxes handles education credits well? My 1098-T has some scholarship money listed on it too and I'm not sure how that affects things.

Cash App Taxes definitely handles education credits well! It walks you through determining which education credit (American Opportunity or Lifetime Learning) is best for you based on your situation. For scholarships on your 1098-T, it will guide you through which portions might be taxable vs. non-taxable depending on what the money was used for (tuition vs. room and board, etc.). The interface asks clear questions to help sort this out - much more straightforward than you'd expect. Their help articles explain things in simple terms too if you get confused at any point.

This! I used this last year and got TurboTax completely free. They hide this option when you go directly to their websites.

Exactly! These companies deliberately hide their free offerings that they're required to provide through the IRS Free File program. It's called "dark patterns" in website design - they make the truly free versions hard to find if you go directly to their sites, then trick you into their paid versions. Always start at the official IRS Free File page (irs.gov/freefile) and click through from there. That way you're guaranteed to get the truly free version if you qualify based on income. Saved me $80 last year for essentially the same exact service.

Do you know if this works if you used the free version? I always use different free services each year depending on which one will let me file for free, so I'm not sure if they save returns for the free users.

Yes, it generally works even with the free versions! I've used the free version of TurboTax for years, and they still save all my returns. The only difference is how long they store them - some free versions might only keep them for 3 years while paid versions might store them for 7+ years. Even if you used different services, it's worth checking all of them. Just make sure you're logging in with the same email you used when you filed in 2020. Sometimes people forget which email they used for tax services.

This worked for me! My return kept getting rejected and I was panicking. Tried the $0 AGI trick and it went through immediately. Thanks for the tip!