One mistake I see a lot - make sure your properties actually qualify as short-term rentals for tax purposes. Its not just about being on Airbnb. The average stay needs to be less than 7 days, and you need to be providing substantial services (similar to hotels). Also remember that material participation for each property is determined separately unless you make a grouping election. If your spending 600 hours combined across all properties, but only 150 on one of them, that specific property might not qualify as active without proper grouping.

Great question about the 7-day average and substantial services! The IRS looks at several factors to determine if you're providing "substantial services" similar to a hotel: - Daily housekeeping or frequent cleaning (you've got this covered) - Providing linens, towels, and toiletries (check) - Concierge-type services like local recommendations, booking activities - Maintenance and repair services - Guest communication and problem resolution Based on what you mentioned (linens, toiletries, coffee, cleaning between guests), you're likely meeting the substantial services test. The key is that these services are provided for the convenience of the occupant, not just basic property maintenance. For the material participation piece that Laura mentioned - you're absolutely right about the grouping election. With 600-700 total hours across multiple properties, Ethan should definitely consider making an election to group his rental activities together. This allows him to meet the material participation test for the entire grouped activity rather than each property individually. The election needs to be made by filing a statement with your tax return, and once made, it's generally binding for future years unless there's a material change in circumstances.

Has anyone dealt with dissolving an S-Corp that had PPP loans or EIDL during covid? We got both and I'm not sure if that affects the dissolution process at all.

I went through S-Corp dissolution in Texas last year and want to echo what others have said - your accountant's advice is incorrect on both counts. You can dissolve an S-Corp at any time during the year, not just at year-end. And you absolutely cannot skip quarterly filings just because you're planning to dissolve. Here's what I learned the hard way: even if you're losing money, you may still have employment tax obligations (payroll taxes, unemployment insurance) that continue until the business is officially closed. Missing these can result in penalties that accrue daily. The dissolution process itself took me about 10 weeks from start to finish. I had to file with both the state and IRS, settle all outstanding obligations, and issue final K-1s to shareholders. The final tax return covered the period from January 1 to the dissolution date. One thing that caught me off guard was that even though we had losses, there were still some tax implications when we distributed the remaining assets (mostly office equipment) to shareholders. Make sure you understand the tax consequences before you start the process. My advice would be to get a second opinion from a tax professional who specializes in business dissolution, or use one of the resources others have mentioned to get proper guidance. Don't let this drag on - the sooner you start the proper process, the sooner you'll be done with all the filing requirements.

Has anyone had luck getting an IP PIN with a foreign address? I'm an expat living abroad and can't get past the address verification step in the online system. The international IRS number is even harder to get through on than the domestic one.

I went through this exact same nightmare last year! What worked for me was creating an IRS online account first at irs.gov/account. Once you have that set up, you can access the "Get an IP PIN" tool more easily. The key thing that helped me was having my prior year tax return handy - you'll need the exact AGI (Adjusted Gross Income) from line 11 of your 2023 Form 1040. Also make sure you're using a phone number that's been in your name for a while, as that's part of their verification process. If the online verification fails (which happens to about 30% of people), don't panic! You can still call the IP PIN hotline at 800-908-4490, but try calling right when they open at 7 AM EST - that's when you have the best chance of getting through quickly. I got through in about 20 minutes when I called first thing in the morning. The $3,200 refund should still come through fine once you get your PIN and file. The IRS actually processes refunds pretty quickly once they receive a complete return - usually within 21 days. Good luck!

As someone who's made ISO mistakes before, I strongly recommend keeping a spreadsheet with all your grant dates, exercise dates, fair market values, and exercise prices. It's easy to lose track, especially if you have multiple grants or partial exercises. Also, don't forget about state taxes! Everyone focuses on federal, but states have different rules for how they treat ISO dispositions.

This is such a timely discussion! I just went through this exact situation last month. One thing that really helped me was understanding that the "disqualifying disposition" ordinary income treatment only applies to the spread at exercise, not the entire gain. So in your case, Mateo, if you sell now for $42,000 and you paid $12,000 for shares worth $35,000 at exercise, here's what happens: - The $23,000 spread at exercise becomes ordinary income (taxed at your regular income rate) - The additional $7,000 gain ($42,000 - $35,000) is treated as short-term capital gains This is different from a qualifying disposition where the entire $30,000 gain ($42,000 - $12,000) would be long-term capital gains. Also, don't forget you may have already triggered AMT liability when you exercised in March 2024, regardless of whether you sell now or later. That $23,000 spread was an AMT preference item in 2024. The decision really comes down to: pay ordinary income rates on $23,000 now + short-term capital gains on $7,000, versus waiting and potentially paying long-term capital gains rates on the full $30,000 (assuming the stock price holds).

Make sure to also check if you need an ITIN (Individual Taxpayer Identification Number) or EIN (Employer Identification Number) for your business. You'll definitely need one of these to file any US tax forms.

As someone who went through this exact process last year with my international marketplace, I'd strongly recommend getting professional help rather than trying to handle this yourself. The compliance requirements are incredibly complex and change frequently. Beyond what others have mentioned, you'll also need to consider: 1. **Information reporting requirements** - You may need to file Forms 1099-K for US vendors who exceed certain payment thresholds ($600 for 2024) 2. **Backup withholding** - If vendors don't provide proper tax documentation (W-9 forms), you might need to withhold 24% of their payments 3. **State economic nexus laws** - These vary significantly by state and some have very low thresholds (South Dakota is just $100K in sales OR 200 transactions) 4. **Treaty benefits** - Depending on your home country, you might be able to reduce or eliminate certain US tax obligations through tax treaties The penalty structure is also quite severe - states can impose penalties of 25% or more of uncollected taxes, plus interest. For a growing business, getting this wrong upfront can be financially devastating. I'd recommend starting with a comprehensive analysis of your specific situation before making any moves. The investment in proper guidance upfront will save you significantly more in penalties and corrections later.