I'm dealing with a similar situation with my vacation rental and this thread has been incredibly helpful! Based on what I'm reading, it sounds like the key is first determining whether your property falls under the 7-day rule (making it a business activity) or if it's a traditional rental activity. For traditional rental activities with longer average stays, the active vs passive participation distinction matters a lot for the $25,000 loss allowance. But for short-term rentals with average stays of 7 days or less, you're looking at material participation tests instead since it's considered a business activity. One question I still have - if you have multiple short-term rental properties, do you evaluate the participation tests for each property individually, or can you combine your activities across all properties? I manage three different Airbnb units and I'm not sure if my management time gets pooled together or evaluated separately for each property.

This is such a helpful discussion! I'm in a similar boat with my mountain cabin rental and the distinction between active vs passive participation has been driving me nuts too. What really helped me was tracking all my management activities in detail - even the time spent reviewing financial reports, approving repairs, and communicating with the property management company. I realized I was doing way more "active participation" work than I initially thought. One thing I learned the hard way is that the average rental period calculation is crucial. My cabin has some week-long rentals mixed with weekend stays, so I had to carefully calculate the average to determine if the 7-day rule applied. It turned out my average was 8 days, so I stayed in the traditional rental activity category where active participation mattered for the $25k loss allowance. The income phase-out is also something to watch carefully - if you're close to that $100k-$150k range, it might be worth timing some income or deductions to maximize your rental loss deduction eligibility.

Anyone else find that these tax software options don't handle the health insurance deduction for S Corp owners very well? That's been my biggest frustration with TaxAct.

I switched from TaxAct to TurboTax for our S Corp last year and it was definitely worth it! Like you, I was getting frustrated with TaxAct's outdated interface. TurboTax handles the S Corp passthrough income much more smoothly - especially the flow from the business return to personal. The interview process walks you through everything step by step, which helped me catch some deductions I'd been missing (like properly calculating the home office percentage for business use). One specific advantage: TurboTax does a better job explaining the reasonable salary requirements for S Corp owners taking distributions. This is crucial since the IRS scrutinizes this area heavily with 1099 income flowing through S Corps. The price difference is noticeable, but given that you're already doing the accounting work yourself, the time savings and reduced stress during tax season made it worthwhile for us. Plus their customer support is significantly better if you run into issues. If you're comfortable with tax concepts already, you might also want to double-check your past returns to make sure you haven't missed anything over the years with TaxAct's less intuitive interface.

I file taxes for my husband's s-corp and we have a sept 30 fiscal year. I was told to use tax software from the CALENDAR year when the fiscal year ENDS. So for a july 1 2021 - june 30 2022 fiscal year, we used 2022 tax software even though we filed in september 2022. This has always confused me but our accountant says its right. just be careful cause the forms change yearly!!

Just wanted to add one more important detail that might help other newcomers like myself - make sure you're aware of the estimated tax payment deadlines for fiscal year S-Corps too! For a June 30 fiscal year end, your quarterly estimated payments are due on September 15, December 15, March 15, and June 15. This was another area where I initially got confused because I was thinking in calendar year terms. Also, if you're new to handling S-Corp taxes, I'd strongly recommend getting professional help at least for the first year or two. The interplay between the corporate return (1120-S) and the individual K-1 reporting can get complex, especially with fiscal years. Better to invest in proper guidance upfront than deal with penalties or corrections later!

Make sure you keep all documentation related to the settlement in case of an audit! I had a similar situation and the IRS questioned it three years later. Having the settlement agreement and evidence of the payment saved me from a huge headache. Also consider if any portion of the settlement was for attorney fees (even if you represented yourself) as there might be some deduction possibilities.

Just went through something similar last year. One thing to watch out for - if your settlement was over $600, the company is supposed to issue you either a 1099-MISC or include it on a corrected W-2, but many don't follow through properly. Don't wait for them to send the forms - you still need to report the income even without receiving the proper tax documents. I'd recommend reaching out to your former employer's payroll department to ask how they're reporting the settlement payment to the IRS. This will help you report it consistently. If they say they're not issuing any forms (which happened to me), document that conversation and report it as "Other Income" as others have mentioned. The key is being proactive since employers often drop the ball on settlement tax reporting.

Quick question - does anyone know if there's a minimum amount of capital gains that requires reporting for F1 students? I made like $200 from stocks this year and wondering if I even need to bother with all this Schedule D stuff.

Just to clarify one more point that might be confusing - while everyone is correctly saying to use Schedule D for your capital gains, make sure you understand that as an F1 student filing Form 1040NR, you'll be using Schedule D-NR (the nonresident version), not the regular Schedule D that US residents use. The calculation process is essentially the same, but Schedule D-NR has some specific instructions for nonresidents. Your $720 gain from $5,800 in stock sales would definitely need to be reported using this form, and then the net gain would transfer to your 1040NR. Also, keep good records of your cost basis and sale dates - you'll need those details for the Schedule D-NR. Don't let your friend convince you to use Schedule NEC, that's definitely for contractor/freelance income, not investment gains.