Has anyone used TurboTax to properly report options trades with wash sale considerations? Last year I had a similar situation and TurboTax seemed completely confused by it when I imported my trading records.

Based on my understanding of the wash sale rules and options trading, you should be fine in your situation. Since you sold call options (wrote calls) rather than bought them, and you're letting them expire, this doesn't establish a new position in the underlying security that would trigger a wash sale. The wash sale rule is designed to prevent taxpayers from claiming artificial losses while maintaining substantially the same economic position. In your case, you sold the stock at a loss and are exiting your options position entirely by letting the calls expire. This is actually moving you further away from the stock, not maintaining exposure to it. Just make sure you don't buy back into the same stock or purchase call options on it within 30 days of your original sale, and you should be able to claim that $1,800 loss without any issues. The key is that you're completely exiting the position rather than trying to maintain exposure while claiming the tax benefit.

Just a quick question for all of you who've dealt with this - which tax software did you use to file with a foreign spouse's ITIN? I used TurboTax last year and it was a nightmare with the ITIN application. Looking for something better for 2023 taxes.

I went through almost the exact same situation with my husband's ITIN application last year. The CP565 followed by CP567 is frustrating but surprisingly common. In our case, the rejection was due to a mismatch in how his birth country was listed - I had put "Republic of Korea" on the W-7 but his passport showed "Korea, Republic of" and apparently that tiny difference was enough to trigger a rejection. The key thing to understand is that your 2022 return is completely safe and processed. The ITIN they assigned is in their system and won't be retroactively invalidated. However, you'll need to resolve this before filing your 2023 taxes. Here's what worked for us: I called the ITIN unit and they explained the exact discrepancy. Then I submitted a corrected W-7 marked as "reapplication" with the original ITIN number referenced, included a copy of both the CP565 and CP567 notices, and provided fresh certified copies of all documentation with the exact spelling/formatting from the passport. The whole process took about 8 weeks to get the corrected approval. Don't stress too much - this is fixable and your current tax situation is secure!

Has anyone tried putting rentals in a C Corporation instead? I've heard mixed things about this approach too.

I think there's some confusion in your research about the "Passive Investment Tax." You might be mixing up a few different tax rules here. The 21% tax rate you mentioned sounds like you're thinking of the corporate tax rate, but that doesn't apply to S Corps since they're pass-through entities. What you might be concerned about is the Net Investment Income Tax (NIIT) at 3.8%, which can apply to passive rental income for high earners. The bigger issue with S Corps for rental properties is actually the opposite problem - you'd likely be required to pay yourself a "reasonable salary" for any active management work you do, which means paying employment taxes (Social Security/Medicare) on that salary. This often makes S Corps less attractive for rental activities, not more. For most rental property owners, an LLC taxed as a partnership or disregarded entity is usually more tax-efficient. You avoid the salary requirements of S Corps while still getting pass-through taxation and the ability to deduct rental losses against other income (subject to passive activity rules). Before making any entity changes, I'd strongly recommend running the numbers with a CPA who specializes in real estate taxation. The "S Corp saves taxes" advice floating around online often doesn't account for the specific complications that rental income creates.

Make sure you're entering Form 5498-SA information in the right place in TurboTax! I had this exact issue. When you get to the HSA section, there's a question that asks something like "Did you make contributions to your HSA outside of payroll deductions?" Answer yes to that. Then it should ask for contributions not reported on your W-2. That's where you enter the amount from the 5498-SA that isn't shown on the W-2. TurboTax will calculate the deduction for you on Form 8889.

I went through this exact same confusion last year! The key thing to understand is that HSA contributions can be made in different ways, and each affects your tax forms differently. If your wife's HSA contributions don't show up in box 12 of her W-2, it's likely because either: 1. She made direct contributions to her HSA (not through payroll), or 2. Her employer made the contributions directly as a benefit For TurboTax, you need to navigate to the HSA section under "Deductions & Credits" and look for something like "HSA contributions not on W-2" or "Did you make HSA contributions outside of payroll?" This is where you'll enter the amount from her 5498-SA form. The 5498-SA shows all contributions made to the HSA during the year, but only certain types need to be claimed as deductions. If they were direct contributions (not through payroll), you can deduct them. If they were employer contributions, they're already tax-free and don't need to be deducted. Check her paystubs to see if HSA amounts were deducted from her paycheck. If not, they were likely either direct contributions she made or employer contributions. This will help you determine how to handle them in TurboTax.

While you're waiting to get home, it might be worth checking your IRS account online. You can create one at irs.gov/account and it shows any outstanding balances, notices sent, and payment plans. Might give you some peace of mind without having to open the letter.

Glad to hear it turned out to be good news! This is actually a great reminder for everyone - the Bureau of the Fiscal Service handles both incoming AND outgoing payments, so their letters aren't always bad news. That Philadelphia address is indeed commonly used for refund notifications and treasury payments. For future reference, you can usually tell the difference by looking at the envelope itself - collection notices typically have more urgent language like "IMPORTANT TAX NOTICE" or "FINAL NOTICE" prominently displayed, while refund notifications are usually more neutral in their presentation. Your experience is pretty common - the IRS does periodic reviews and sometimes catches deductions or credits that taxpayers missed, especially when tax laws change retroactively. Enjoy that unexpected $843!