If I open an HSA account now in 2024, can I still make a contribution that counts for 2023? My employer offered a high-deductible plan that I was enrolled in all of 2023, but I never set up the HSA. Would really help if I could still get that AGI reduction.

Yes, you absolutely can! As long as you were enrolled in a qualified high-deductible health plan (HDHP) during 2023, you can open an HSA now and make contributions for the 2023 tax year until the tax filing deadline (April 15, 2024). Since you were enrolled in the HDHP for the entire year, you can contribute the full amount - $3,850 for individual coverage or $7,750 for family coverage. Just make sure to designate it as a 2023 contribution when you make it. This will reduce your 2023 AGI by the full contribution amount. It's one of the few retroactive tax moves you can still make this year to affect last year's taxes.

The Qualified Business Income Deduction (Section 199A) is a bit confusing position-wise. Technically, it doesn't reduce your AGI - it's actually taken after your AGI is calculated but before your taxable income is determined. It's similar to the standard or itemized deduction in that regard. So while it's an amazing deduction that can reduce your taxable income by up to 20% of your qualified business income, it unfortunately won't help lower your AGI for things that are AGI-dependent. Focus instead on retirement contributions, HSA, and other above-the-line deductions to reduce your actual AGI.

Is there a way to check if someone is a legitimate tax preparer before hiring them? Like a database or something?

Yes, you can verify if someone has a valid PTIN through the IRS. While the IRS doesn't have a public database you can search, you can ask to see their PTIN certificate or card before working with them. Legitimate preparers will have this readily available. You can also check if they're a CPA (through your state's board of accountancy), an Enrolled Agent (through the IRS), or a member of professional organizations like the National Association of Tax Professionals or the National Association of Enrolled Agents.

OMG that's terrifying! Did you ever get it resolved? Did you have to pay penalties?

Do you have to have a certain amount of tax debt to qualify for the Fresh Start stuff? I owe about $8,500 from 2022 and 2023... is that even enough to bother with these programs?

There's no minimum debt requirement for the Fresh Start provisions, so your $8,500 definitely qualifies. For smaller debts like yours, you might especially benefit from the streamlined installment agreement option, which has simplified application requirements for debts under $50,000. With $8,500, you might also consider whether you have any means to fully pay the debt, such as a personal loan with a lower interest rate than the IRS charges. The IRS interest and penalties continue to accrue even while you're on a payment plan, so sometimes it makes financial sense to pay it off another way if possible. But if that's not an option, definitely look into the streamlined installment agreement.

This sounds like you're advising tax evasion which is literally a crime. You should ALWAYS file your tax returns even if you can't pay. Not filing is way worse than filing and setting up a payment plan.

We don't have any side businesses, but we do have some investments that probably didn't have withholding. And we're not homeowners yet so no mortgage interest. Do retirement contributions through our employers' 401k plans automatically reduce our taxable income or do we need to do something special to claim that?

401k contributions through your employers should automatically reduce your taxable income - they're taken out pre-tax so they already lowered the W-2 income reported to the IRS. You don't need to do anything special to claim those. If you have investment income without withholding, that's likely contributing to your tax bill. For the future, you might want to make quarterly estimated tax payments on that income, or increase your W-4 withholding to cover it. The key is making sure you're paying enough tax throughout the year one way or another.

I use TurboTax Premium and it does have a W-4 calculator that can help with this. After you complete your return, it offers to help you update your W-4 for next year based on your results. It's pretty helpful but honestly I still found it confusing when dealing with two incomes.

Do you need specific forms from your school to claim the Lifetime Learning Credit? My university gave me a 1098-T but it doesn't show all the details I think I need.

Yes, you should receive Form 1098-T from your US university which shows your qualified education expenses. Sometimes it doesn't include everything that's actually eligible though! For example, my form didn't include my required course materials, but those are qualified expenses I could add. If you're missing information on your 1098-T, contact your university's bursar or financial office - they can usually provide an itemized statement of your expenses. Keep receipts for things like textbooks and required supplies too, since those count but might not appear on your 1098-T.

I used TaxAct last year and it asked clear questions about my education history that helped determine I was only eligible for Lifetime Learning Credit. It specifically asked if I had completed 4 years of post-secondary education before, not just if I had claimed AOTC before.

Thanks for the recommendation! I'll check out TaxAct. The software I was using just kept asking if I'd claimed AOTC for 4 years already, not whether I'd completed 4 years of college, which was confusing since I never claimed it before (wasn't in US during undergrad).