Has anyone wondered if the "regularly and exclusively" rule has ANY exceptions? Like what if I have a small apartment and literally have no choice but to use my work computer on the kitchen table sometimes? The IRS rules seem designed for people with huge houses where dedicating an entire room is possible.

I'm dealing with a similar situation but from a slightly different angle - I'm a freelance graphic designer working from our studio apartment, and I've been really careful about the "exclusive use" requirement since I got burned on this before. What I ended up doing was creating a very specific work zone using a room divider screen (got it cheap on Facebook Marketplace) to physically separate my desk area from the rest of our living space. This way there's a clear visual boundary that shows the IRS this space is exclusively for business use. I also keep a simple work log noting when I'm using the space vs when I'm at client offices or cafes. My CPA said this documentation helps prove the "regular" part of "regular and exclusive use" - showing that I consistently use this space for work, not just occasionally. One thing that might help your situation: since your girlfriend only uses the desk "occasionally" when you're not there, you could try setting up a schedule or system where that space is clearly yours during defined work hours. The key is being able to demonstrate that during your business hours, that space is exclusively yours for work purposes.

Hey just FYI, don't forget about basis adjustments for things like business loans and asset purchases. They can really mess up your calculations if you don't account for them properly. I learned this the hard way last year.

This is a great discussion and really helpful for understanding S corp distributions! I'm in a similar situation with my single-member S corp and was getting confused about when distributions become taxable. One thing I'm still unclear on - if I have positive basis at the beginning of the year but take distributions that exceed my basis during the year, do I calculate the capital gains on a transaction-by-transaction basis or just at year-end? For example, if I start with $20K basis, have $10K income during the year, but take $40K in distributions spread throughout the year, are the last $10K of distributions automatically capital gains, or do I only know at year-end after accounting for all income and distributions? Also, does the timing of when during the year I take distributions matter for this calculation?

Don't forget that if you buy tools that cost more than $2,500 each (like some of the nicer diagnostic equipment), you'll need to depreciate them over several years instead of deducting them all at once. That mechanic with $500k in tools definitely didn't write them all off in one year. Also, keep a log of how you use each tool specifically for your work. If you ever get audited, the IRS loves to reclassify "business" tools as personal if you can't prove they're primarily for work use. Take photos of the tools in your work environment too.

When I started driving, I made the mistake of buying a bunch of tools without keeping good records. Can confirm it was a HUGE headache come tax time. Now I keep a separate credit card just for work expenses and take pictures of all receipts with a note about what the tool is for. One thing nobody mentioned - if you work across multiple states (which most truckers do), the state tax deduction stuff gets complicated fast. I ended up paying a tax pro last year just to sort out which states I could claim what deductions in. Was worth it though, saved about $700 compared to what I would have filed on my own.

Don't forget about the Earned Income Tax Credit! If you're a stay-at-home parent with 3 kids and only one income, the EITC can be substantial. Getting married might change your eligibility or the amount you receive. When we were making around $80k with 2 kids, we found that staying unmarried actually gave us a bigger combined refund because of how the EITC worked for us.

I'm in a very similar situation and just went through this analysis myself! One thing that really helped me was using the IRS's own withholding calculator at irs.gov to compare scenarios. It's free and official, so you know the calculations are accurate. With your income level ($95k) and 3 kids, you're likely to benefit from marriage because: 1) The Child Tax Credit ($2,000 per child) has higher income phase-out thresholds for married filing jointly 2) Your boyfriend's Head of Household status is good, but Married Filing Jointly standard deduction for 2024 is $29,200 vs $21,900 for HOH 3) The mortgage interest deduction he gets from the home purchase will still benefit you both when married However, definitely check if you're currently receiving any means-tested benefits like SNAP, WIC, or Medicaid. Sometimes the tax savings don't outweigh the loss of benefits. I'd also suggest running the numbers for both 2024 AND 2025 tax years, since some credits and thresholds change annually. We found that while marriage helped us in 2024, it might not be as beneficial in 2025 due to some expiring provisions. Good luck with your decision!

Quick question for anyone using OLT for non-resident filing - does it handle multiple 1099s? I have one from Robinhood, one from Webull, and another from TD Ameritrade (all with different wash sales and dividends). Wondering if I need to combine these somehow or if the software can handle multiple investment accounts.

As someone who's navigated the non-resident alien tax maze with investment income, I feel your pain! Here are a few additional tips that might help: 1. **Double-check your substantial presence test** - Make sure you actually qualify as a non-resident alien for tax purposes. Sometimes students think they're non-resident when they might actually be resident aliens for tax purposes after being in the US for multiple years. 2. **Consider the treaty benefits** - Depending on your home country, there might be tax treaty provisions that could reduce your tax liability on investment income. Check if your country has a tax treaty with the US. 3. **Keep detailed records** - Document all your trades, especially the wash sale transactions. The IRS may ask for supporting documentation, and having everything organized will save you headaches later. 4. **State tax considerations** - Some states don't tax non-resident investment income at all, while others have different rules than federal. Research your specific state's requirements. The Free File options mentioned above are definitely worth trying first given your budget constraints. If those don't work out, you might also check if your university's international student services office has any tax preparation assistance or recommendations for affordable services that specialize in non-resident returns. Good luck with your filing!