Make sure you've considered your basis allocations too! I made a huge mistake in a similar transaction. Had bought my property+business for $350k years ago, but never properly allocated the purchase price between land, building, and business assets. When I sold, my accountant had to reconstruct everything to figure out my adjusted basis in each component. Ended up paying way more tax than necessary because I couldn't properly document some improvements I'd made to the building. So beyond just the allocation of the sale price, make sure you've got your cost basis properly allocated too!

One thing that hasn't been mentioned yet - if you're doing a 1031 exchange on the real estate portion, make sure you understand the "net equity" rule. You need to purchase replacement property of equal or greater value AND put the same amount or more of equity into the new property to defer all the capital gains. So if you're allocating $800k to real estate and you had, say, a $300k mortgage that was paid off at closing, you'd need to put at least $500k equity into your replacement property. A lot of people get tripped up thinking they just need to buy something worth $800k, but if they finance more of the new purchase, they could end up with taxable "boot." Also, since you mentioned the booming real estate market in your area - remember you have to identify your replacement property within 45 days of closing, and that clock doesn't stop ticking. In hot markets, properties can go under contract quickly. Consider identifying multiple properties in case your first choice falls through.

This is super frustrating but unfortunately pretty common during busy filing seasons. Since you e-filed and have confirmation, your return is almost certainly in their system - it's just a timing/processing issue. The non-filing letters are often generated automatically before their systems sync up. I'd recommend calling the IRS directly with your confirmation number to get them to update your account status. Also keep all your filing documentation just in case you need to prove you submitted on time. Usually resolves within a few weeks once they catch up on processing.

Ugh, this is so stressful when it happens! I went through something similar a couple years back. The IRS systems can be really slow to sync up, especially during peak filing season. Since you e-filed and have confirmation, your return is almost definitely in their system somewhere - it's just caught in processing limbo. I'd recommend calling them with your confirmation number and asking them to manually check if they received it. Also, if you need proof of filing for anything urgent (like financial aid or loan applications), your e-file confirmation should work as temporary documentation until this gets sorted out. Hang in there!

Has anybody had issues with TurboTax handling this property tax situation correctly? My payment got delayed into January 2023 for my 2022 taxes, and TurboTax kept trying to put it on 2022 because of how I entered it.

Just wanted to share my experience since I dealt with something very similar! I had property taxes that were due in December 2022 but didn't pay them until February 2023. I was so stressed about which return to file them on. After doing some research and calling my tax preparer, I confirmed what others have said here - it's definitely the year you made the payment that matters. So your $4,200 property tax payment goes on your 2023 return since that's when you actually paid it. One thing that helped me feel more confident was keeping really good records of the payment date. I saved the bank statement showing the payment date, the receipt from the tax office, and even took a screenshot of my online payment confirmation. This way if there are ever any questions, I have clear documentation of exactly when the payment was made. Don't beat yourself up about missing the original due date - life happens! The important thing is you're getting it sorted out correctly now.

Has anyone had the UK tax authorities reach out about EIS investments when you're not a UK tax resident? I invested in several companies through Crowdcube with EIS certificates but since I don't pay UK taxes (I'm a US citizen in France), I didn't claim any UK tax benefits. Still got emails about my EIS certificates though.

I'm dealing with a similar situation as a US citizen living in Italy who invested through both Crowdcube and Seedrs last year. One thing I learned the hard way is that you need to keep detailed records of each investment's structure and the underlying business activities, not just the total amounts invested. For reporting purposes, I created a spreadsheet tracking each company I invested in, their primary business activity, revenue sources, and investment structure. This helped me determine which ones might have PFIC issues (spoiler: most didn't, but one property development company was borderline). Also, don't forget that if any of these investments pay dividends or if you sell shares, you'll need to report that income on your US taxes. The UK won't withhold taxes for non-residents in most cases, but you still owe US taxes on the income. Keep good records of any foreign taxes paid too in case you can claim foreign tax credits. The EIS certificates are basically irrelevant for us as US taxpayers - we can't use the UK tax benefits, but the certificates do provide useful documentation about the nature of the investment for US reporting purposes.

One thing no one has mentioned yet - did you check if your broker has any residual cash from the company's wind-down? Sometimes when companies fold, there's a small liquidation distribution that gets sent to your brokerage account. You'll want to account for that as it reduces your loss slightly. Also, check if your shares were held in a custodial account somewhere. Even though the company is gone, the shares might still be reflected in some brokerage account, which would make documentation easier.

Has anyone considered the impact of the ESPP discount on your cost basis? When you participate in an ESPP, you often get shares at a discount to market value. That discount is generally considered compensation income. For example, if the fair market value was $100 per share but you paid $85 through the ESPP (15% discount), that $15 discount should have been reported as income on your W-2 in the year of purchase. Your actual cost basis would then be $100 ($85 paid plus $15 reported as income). This could affect how much loss you can claim now that the shares are worthless.