Has anyone used health insurance premiums as a deduction while traveling? I'm paying for a global health insurance plan that covers me in all countries ($370/month) and wondering if that's fully deductible as self-employed.

Great thread! As someone who's been doing the digital nomad thing for 3 years, I'd add a few more deductions that might apply to your situation: **Equipment depreciation** - If you buy a laptop, camera, or other business equipment while traveling, you can depreciate it over several years or take the Section 179 deduction for the full amount in year one (up to certain limits). **Professional memberships and subscriptions** - Any industry associations, professional development platforms, or business-related subscriptions are fully deductible. **Banking and payment processing fees** - International transaction fees, wire transfer costs, and payment processor fees (PayPal, Stripe, etc.) are all business expenses. **Legal and professional services** - Tax prep, business formation costs, contract reviews, etc. **Travel between client locations** - While personal travel isn't deductible, if you're traveling specifically to meet clients or for business purposes, those costs can be deducted. One thing that helped me was opening a dedicated business checking account and putting ALL business expenses on a business credit card. Makes tracking so much easier come tax time. Also, consider using apps like Expensify or similar to photograph receipts immediately - you'll thank yourself later! The Foreign Earned Income Exclusion is definitely worth pursuing if you can hit those 330 days. At your income level, it could eliminate most of your federal tax liability.

Just a quick tip: make sure you keep proof of when you file! Even if there's no penalty, it's good to have documentation showing you filed as soon as you realized the mistake. Take screenshots of your filing confirmation or save the email receipt. I had an issue a couple years ago where the IRS claimed they never received my return even though I filed electronically. Having the confirmation email with date and time stamp saved me a huge headache.

Don't panic - you're in a much better situation than you think! Since you're expecting a refund of around $870, there are absolutely no penalties for filing late, even past the extension deadline. The IRS only penalizes late filing when you owe them money. That said, definitely file this weekend as planned. While there's no penalty, you're essentially giving the government an interest-free loan of your refund money. Plus, you want to get it done before you forget again or lose any documents. For your multi-state situation with the job change and move, TurboTax should handle it well. Just make sure you have all your W-2s from both states and any documentation related to your move - some moving expenses might be deductible depending on your situation. The key thing is to file accurately rather than rushing. Take your time to make sure you capture all your income sources and potential deductions from your move and job change. You've already waited this long, so a few extra hours to do it right won't hurt.

Has anyone noticed PayPal's new reporting requirements? I think they're sending 1099-Ks for much smaller amounts now which means the IRS is getting more visibility into these transactions anyway.

I've been dealing with this exact situation for my consulting business. One thing to keep in mind is that you should also save screenshots or records of the PayPal transaction details showing the breakdown of the payment and fees. This documentation will be helpful if you ever get audited, since it clearly shows the $1250 you paid for services versus the $40 PayPal fee. I learned this the hard way when my accountant asked for detailed records during tax prep last year. Also, make sure you're consistently handling all your PayPal transactions the same way - don't mix and match reporting methods or it could raise red flags.

Does anyone know if Venmo or PayPal payments count as "cash" for Form 8300? I have some clients who prefer to pay that way and sometimes the amounts are over $10k.

This is really helpful information! I've been running a small business for about two years now and honestly had no idea about the distinction between different payment types for Form 8300. I've been getting direct deposits and checks from clients, with some payments over $10k, and was worried I might have missed filing requirements. It's reassuring to know that electronic transfers don't count as "cash" for this form. I was starting to panic thinking I might owe penalties for not filing forms I didn't even know I needed to file! One question though - if a client pays part of an invoice with a wire transfer and part with actual cash (like if they wanted to use up some physical currency they had), and the total is over $10k, would I need to report just the cash portion or the entire combined payment?

Have any of you run into issues with reasonable compensation analysis in this situation? Our company's CPA keeps warning us that the IRS might challenge our arrangement if my salary as an employee seems too low compared to the profits distributions I receive as a member.

This is a really insightful discussion! I'm dealing with a similar situation where I received profits interests in my company earlier this year. One thing I haven't seen mentioned yet is how this affects quarterly estimated tax payments. Even though my regular salary continues to have proper withholdings as a W-2 employee, I'm wondering if I need to start making quarterly payments for the profits interest portion. Since there won't be any withholding on potential K-1 distributions, I'm concerned about underpayment penalties if the company has a profitable year. Has anyone had to adjust their estimated payments after receiving profits interests? I'm trying to figure out if I should start making quarterlies now or wait until I actually receive distributions to see what the tax impact will be.