Quick question related to this - if the OP is getting 1099s from both contract work and ticket sales, does he need to file two separate Schedule Cs or can they be combined since they're both independent contractor type income?

Great thread with lots of helpful info! As someone who's been navigating 1099 contractor taxes for a few years now, I'll add a couple practical tips that might help: For your business exploration expenses - definitely keep detailed records showing your profit motive. I learned this the hard way when I got questioned about some photography equipment purchases. What helped me was creating a simple business journal documenting my activities: dates I worked on the business, what I did, expenses incurred, and income generated. Even failed attempts count if you can show genuine business intent. One thing I wish someone had told me earlier: if you're testing multiple business ideas, consider whether some of them might actually qualify as research and development expenses rather than just business expenses. The tax treatment can sometimes be more favorable. For the ticket reselling - definitely agree with the separate Schedule C advice. I made the mistake of lumping different income streams together my first year and it was a nightmare to untangle. Keep meticulous records of every ticket purchase with the intent to resell, even if you end up using some personally. Also, don't forget about the quarterly estimated tax payments if you're making decent money from both activities. Getting behind on those can be painful come April!

Quick tip from someone who handles HSA compliance professionally - the "reasonableness" standard for excess contribution calculations means you won't get in trouble for small discrepancies. The IRS cares much more that you: 1) Remove the excess contribution before the deadline 2) Make a good faith effort to calculate earnings 3) Report the distribution correctly on your taxes Your method is certainly reasonable. I typically recommend simply using the overall account rate of return (total gains/losses divided by average balance) applied to the excess contribution amount.

Don't forget that when you withdraw excess HSA contributions, the earnings portion is taxable as "other income" in the year you make the withdrawal! I learned this the hard way. The excess contribution itself isn't taxed again if you already included it in income (which you would have if it was through your employer's payroll), but the earnings definitely are taxable.

Quick tip: Download IRS Publication 519 (U.S. Tax Guide for Aliens). It has a detailed flowchart on page 8 that helps determine your status. Based on your arrival date, you're almost certainly a nonresident alien for 2024 tax purposes, which means Form 1040-NR. Also, most tax software struggles with nonresident returns. TurboTax and H&R Block can do it but you need their premium versions. Sprintax specializes in nonresident returns and might be easier.

Based on your situation (arriving September 15, 2024, with 107 days of US presence), you'll almost certainly need to file Form 1040-NR as a nonresident alien for 2024. The substantial presence test only counts days in the current tax year plus weighted days from previous years - since you have zero previous years, your 107 days falls well short of the 183-day threshold. However, don't overlook the "first-year choice" that Diego mentioned. If you'll be present for at least 75% of days from your first 31 consecutive days through December 31st, AND you expect to pass the substantial presence test in 2025 (which you likely will), you could elect to be treated as a resident alien for all of 2024. This would let you file Form 1040 instead, which often provides better tax benefits. Calculate both scenarios before deciding - sometimes the additional deductions and credits available on Form 1040 can save you more money than you'd think, even though you'd be taxed on worldwide income (though you probably don't have significant foreign income anyway). The key is getting this right from the start. As others have mentioned, filing the wrong form can lead to IRS notices and amended returns down the road.

Does anyone know if her getting food stamps might disqualify her from being claimed as a dependent? I have a similar situation with my mother-in-law who gets SNAP benefits.

One thing to keep in mind is documenting everything throughout the year, not just at tax time. I learned this the hard way when the IRS questioned my dependent claim for my disabled father. Keep receipts for utilities, groceries, medical expenses, transportation costs, and any other support you provide. Also calculate the fair market rental value of your aunt's home - you can look at similar rental properties in your area or get a rough estimate from online rental sites. This will help you prove you're providing more than 50% of her total support even when accounting for the housing she provides herself. Since you mentioned you've been doing this for 9 months, you should be in good shape for the support test. Just make sure to track everything from now until the end of the tax year so you have solid documentation if needed.

Have you looked into section 280A vacation home rules? If you use the basement AT ALL for personal purposes, even occasionally, you need to be very careful with allocations. You might need to use the days rented vs. days of personal use calculation instead of just square footage.

Your situation is actually quite common and you're being smart to think about this proactively. The fact that you specifically purchased a larger home to accommodate the Airbnb business is a strong indicator of profit motive that would help in any IRS review. A few thoughts on strengthening your position: 1. **Documentation is key** - Keep detailed records of time spent on the business (guest communication, cleaning, maintenance, marketing). This shows it's not a hobby. 2. **Your 40% allocation seems reasonable** if it's based on actual square footage used exclusively for the rental. Just make sure you have a simple floor plan or measurement documentation to support this. 3. **Consider showing some profit in 2025** - Even a small profit would help reset the "hobby loss" clock. Maybe slightly reduce some discretionary expenses or be more aggressive with pricing. 4. **Track improvement efforts** - Document any changes you make to increase profitability (pricing adjustments, marketing spend, property improvements). This shows business intent. The IRS knows rental properties can have legitimate losses, especially in the early years or during market downturns. Your repeated efforts and the fact that this isn't enjoyable work for you both support treating this as a business. Just keep good records and consider making 2025 a profitable year if possible.