Thanks for the heads up on payroll providers! Any specific ones you'd recommend for someone in my situation? Also, did you set up a separate retirement plan when you made the switch?

I've heard good things about Gusto and OnPay from other single-member S-Corps. They're more modern and user-friendly than what I ended up with. A local bookkeeper who specializes in small businesses could also be a good option - sometimes they offer payroll services bundled with bookkeeping. For retirement plans, that's actually one of the big advantages of an S-Corp. I set up a Solo 401(k) which lets me contribute both as the employer and employee. You can potentially put away much more than you could with just an IRA or SEP. With your income level, you should definitely look into this as it can significantly reduce your tax bill beyond just the SE tax savings.

This is so confusing. My tax person told me to just pay health insurance personally and take the deduction. Is that wrong?

Thanks for mentioning that! I've only claimed the American Opportunity Credit for 3 years so far, so I should be eligible for one more year. And yes, I have my enrollment verification and payment receipts saved. I paid online through my student portal in December 2022, and I have the confirmation email and bank statement showing the payment date. Would those be sufficient documentation?

Those records should be perfect! Keep the enrollment verification showing you were a student during Spring 2023, along with your payment confirmation and bank statement showing the December 2022 payment date. That's exactly the documentation you'd need if there were ever questions about your eligibility. Since you've only claimed the American Opportunity Credit for 3 years, you should be eligible for one more year, which is great since it's generally more beneficial than the Lifetime Learning Credit for most undergraduates.

Did you need to send any documentation with your amended return or did you just keep it for your records? I'm in a similar situation where I need to amend my 2022 return to claim education expenses I paid in 2022 for Spring 2023 classes.

Thanks for bringing that up! I actually filed through TurboTax but didn't get an advance. I've decided to go ahead and file the amendment after reading everyone's advice. Since it's such a small amount and taxes were already withheld, I'm going to use my refund for bills as planned and then deal with the amendment next month.

That's a great plan. Since you filed through TurboTax and didn't get an advance, you should be able to easily file the amendment through them as well. They actually have a pretty straightforward amendment process built into the software. Just sign back into your account, select the option to amend your return, and follow the prompts to add the missing W2. The system will recalculate everything and prepare the 1040-X for you. Since taxes were already withheld on that small amount, you're right that it probably won't change your situation much at all.

Yes, they absolutely do have automated matching. Every W2 has a copy that goes to the IRS, and their systems eventually match them against your return. Usually happens a few months after filing season ends. For super small amounts though, I've heard they sometimes have thresholds where they don't bother pursuing it.

My credit union actually has a feature in their app that shows pending direct deposits like 3 days before they post! I saw my tax refund in there before the IRS even updated their status. Maybe check if your bank has something similar?

That's a great point about credit unions and smaller banks - they often show pending transactions earlier than the big banks. Some of the major banks have started adding this feature too. Chase and Bank of America both now show pending direct deposits a few days early in their mobile apps. If your bank doesn't have this feature, another trick is to call their customer service department directly. The representatives often have access to pending ACH information that isn't visible in the online banking portal yet.

IRS2Go shows exactly the same info as the website. I had both and they updated simultaneously. Neither one tells you the actual deposit date until it's basically already happening, which is super annoying.

That's a really good point I hadn't even thought about. I'm in Tennessee - do you happen to know if they have any specific rules about business asset sales that differ from federal?

Tennessee is actually one of the better states for this since they don't have a standard income tax. However, they do have the Hall Income Tax which could apply to certain parts of your sale, though it's being phased out. I'd still recommend checking with a Tennessee tax specialist. Even states without income tax sometimes have surprising ways of taxing business sales through other mechanisms. Better to know ahead of time than find out next April!

I did an installment sale for my auto repair shop in 2023. It definitely helped spread the tax burden across multiple years, which kept me from jumping into a much higher bracket. The downside is you're taking on risk if the buyer defaults. Make sure you have rock-solid security agreements in place!