Thanks for mentioning the Form 8606! Would I need to file that for the tax year when I make the contribution to the Traditional IRA, or for the tax year when I do the conversion to Roth? If I contribute now but don't convert until next year, which tax year would it fall under?

You need to file Form 8606 for the tax year in which you make the non-deductible contribution to your Traditional IRA. This establishes your "basis" (after-tax money) in the IRA. If you contribute now (2023 tax year) but don't convert until next year (2024), you would still report the non-deductible contribution on Form 8606 with your 2023 tax return. Then when you do the conversion in 2024, you'd receive a 1099-R for that tax year, and you'd file another Form 8606 with your 2024 return to report the conversion. This is why keeping good records is so important - you need to track your basis over time, especially if you don't convert immediately after contributing.

I use Fidelity for my backdoor Roth and it's super easy. You can open both account types online in about 10 minutes, and their conversion process is just a few clicks. Never had to call customer service once. They also have good educational resources about the process right on their website.

I did call them actually! They basically just confirmed what the 1098 shows - that the actual payment to the county hadn't been made yet in 2023. They said they could provide a statement showing my escrow contributions, but they were clear that doesn't change when the tax was technically "paid" for IRS purposes. Frustrating but at least consistent with what everyone here is saying.

In TurboTax, the property tax paid will typically import automatically if you have your 1098 imported electronically. If not, you'd enter it manually in the "Deductions & Credits" section under "Home Mortgage Interest and Real Estate Taxes." Look for the section about Form 1098 and it will ask for the amount in Box 11 (which is where property taxes paid by your mortgage company appear).

This is interesting! Would you use Schedule D for this instead of reporting as hobby income? And do you need to keep receipts for everything to prove what you originally paid?

I do customize some of them! I repaint about 30% of the models I sell, and sometimes do minor repairs on vintage pieces. I just wasn't sure if that was enough to count as a "real business" since it's still mostly just for fun. But it sounds like that could help my case?

That definitely strengthens your case! The customization and repairs show you're adding value through your skills and labor, which is a big factor in the business vs. hobby determination. Make sure you document your work process - take before and after photos of your customizations, track the time you spend on each project, and keep receipts for all supplies. Also, consider creating a separate Instagram or Facebook page showcasing your work, even if it's just casual. Having a business presence online is another factor that supports business treatment. You might also want to look into selling at model horse shows or conventions if you don't already - participating in trade shows is another indicator the IRS looks for when determining if something is a business. The key is to show that you're making decisions with the intent to eventually be profitable, even if you're not there yet.

Do you happen to know how long it typically takes for a credit card payment to show up in the IRS system? I need to make a payment ASAP but my electronic withdrawal is scheduled for next week.

In my experience, credit card payments typically take 3-5 business days to show up in the IRS system. However, the payment is considered made on the day you submit it, not when it appears in the IRS records - so you're protected from late payment penalties as long as you complete the transaction by the due date. If your electronic withdrawal is scheduled for next week, I'd recommend making your credit card payment immediately. Even if it doesn't show in the system before the withdrawal date, you can contact the IRS with your confirmation number if there's any issue with double payment. They can always refund overpayments, though it might take some time to process.

Good point about doing the math. Some premium travel cards give effectively 2-2.5% value for points when transferred to airline partners though, which can make it worthwhile even with the fees. I always use my Chase Sapphire Reserve for tax payments specifically because the points are worth more than the fees.

Thanks for the suggestion! I didn't even think about their guarantee. Do you know if their guarantee covers situations like this? And would you recommend going back now or waiting to see if the refund comes through first?

H&R Block's accuracy guarantee typically covers penalties and interest that result from preparer errors. In your case, since you caught the error before the return was finalized, it's a bit different, but they should still help you navigate the refund process. I'd recommend going back now rather than waiting. Explain what happened and ask them to contact the IRS on your behalf to confirm the overpayment will be refunded. They have a professional responsibility to help resolve this since it was their preparer's error. If the manager isn't helpful, you can escalate to their corporate customer service.

This is good advice! Also, check your mail regularly. Sometimes the IRS will send a paper check instead of direct deposit for refunds resulting from corrections or amendments, even if you originally paid electronically. I learned this the hard way when my refund check sat in a pile of mail for weeks.