That's actually a really good idea! I hadn't thought of trying a third one as a tiebreaker. I'll give TaxSlayer a shot tonight and see if it aligns with either Keeper or FreeTaxUSA. I'm guessing if two of them match, that's probably the right calculation? Though with my luck all three will show different amounts lol.

Yeah, exactly - if two match and one is different, that's usually a good indication. And with three states and multiple 1099s, it's worth the extra effort to be sure. Just make sure you're entering everything identically in all three systems. I found sometimes even the order of entering certain forms can affect calculations in weird ways. Let us know which one ends up matching!

In my experience, TurboTax seems to handle the QBI (Qualified Business Income) deduction best for multi-state situations. I had issues with H&R Block last year where it wasn't properly allocating the QBI between states. Maybe try that as your third option?

Thanks for the tip! I didn't want to spend the money on TurboTax since it's so expensive compared to the others, but if it handles QBI better it might be worth it. Definitely seems like that could be part of my issue.

I thought TurboTax and TaxAct only have free versions if your return is super simple? I have investment income and a home office deduction so I always assumed I'd have to pay for the premium versions. Did you have any complex situations on your return?

You're partly right - the completely free versions are limited, but they're more comprehensive than most people realize. I have some dividend income and capital gains, and TaxAct's free version handled those fine. For more complex situations like home office deductions, you might need to use their paid version, but it's still much cheaper than paying an accountant. I found that the Deluxe version was only around $25 when I started with the free version then upgraded only for the features I needed. Completely worth it to avoid the stress of technical glitches like that checkbox issue!

Thanks for this info! One question - do you happen to know if the calculator in the forms is at least smart enough to add this automatically based on birthdate? Or do we need to manually do the math for line 12a?

The calculator doesn't automatically adjust for age or blindness since it relies on those checkboxes working properly. You'll need to manually calculate your standard deduction amount by adding your base standard deduction plus the additional amounts I mentioned. For 2024 taxes, the base standard deduction amounts are $14,600 for single/HOH, $29,200 for married filing jointly. So for example, if you're single and over 65, you'd manually enter $14,600 + $1,850 = $16,450 on line 12a. The system won't do this calculation for you because of the checkbox malfunction.

Do you need to verify those certificates somehow? Or just keep them on file? I've had a few business customers claim they're exempt but I wasn't sure if I should just take their word for it.

You need to collect the actual certificate from them - don't just take their word for it. Most states have specific forms customers need to fill out. You should verify the certificate has all required information (their tax ID number, signature, etc.) and keep it on file. Some states also let you verify tax ID numbers on their websites. You don't need to send these certificates to the state, but you absolutely must have them available if you get audited. I now keep digital copies of all certificates in a dedicated folder so I can find them easily.

I've used both. TaxJar is more affordable for small businesses but Avalara has more features if you're growing fast. With your sales level ($2,500/month), TaxJar's basic plan would probably be sufficient. The time savings is definitely worth it - it automatically files your returns in multiple states and keeps track of all the weird local tax rates.

Wait seriously? I had no idea about the Roth IRA limitation! I thought the income limits were just reduced, not basically eliminated. That's a huge factor to consider...

Yes, it's one of the most restrictive aspects of filing separately that catches people by surprise. The income limit for Roth IRA contributions when filing separately is just $10,000 - after that, you can't contribute at all. It's not a gradual phase-out like with other filing statuses. For comparison, with married filing jointly in 2024, the Roth contribution starts phasing out at $230,000 and completely phases out at $240,000 of modified AGI.

This is the approach we took. My wife is a public school teacher going for PSLF, so we file separately to keep her payments low. Yes, we pay more in taxes each year, but after running the numbers, we'll come out ahead by about $42,000 over the 10-year forgiveness period.

Wait, really? I didn't know that scholarships would reduce the amount I can withdraw penalty-free. My daughter did get about $15K in merit scholarships. So I would need to subtract that from the total expenses before figuring out my penalty-free withdrawal amount?

Yes, that's correct. Any tax-free educational assistance must be subtracted from your qualified expenses before calculating your penalty-free withdrawal amount. This includes tax-free scholarships, Pell grants, employer-provided educational assistance, and veterans' educational assistance. In your case, if your daughter received $15K in merit scholarships, you would subtract that from your total qualified expenses. So if tuition is $80K and other qualified expenses are, say, $10K, your total qualified expenses would be $75K ($90K minus the $15K scholarship) rather than the full $90K.

This is actually an important timing consideration. The IRS requires that the IRA withdrawal occur in the same tax year that you pay the qualified education expenses. If you pay tuition in December 2025 (which is in tax year 2025), but take the IRA withdrawal in January 2026 (tax year 2026), you wouldn't be able to connect those specific education expenses to your withdrawal for the penalty exception.

Thanks for clarifying that! Guess I need to time my withdrawal more carefully than I thought. I'll make sure to take out the money before the end of December since that's when I'll be paying the spring tuition bill.