Thanks for this perspective. I hadn't considered the "round-trip transaction" angle. If I were to actually relocate and live abroad full-time (which I'm planning to do anyway), would that strengthen the legitimacy of this arrangement at all? Or would the IRS still view the structure itself as problematic regardless of my residency?

Actually living abroad full-time would certainly help satisfy the physical presence test for the Foreign Earned Income Exclusion, but it wouldn't necessarily legitimize the overall structure. The IRS would still question why this particular business arrangement is necessary. They'd look at factors like: Does this foreign management company have any employees besides you? Does it manage properties for anyone else? Is the fee structure comparable to what unrelated property management companies charge? Does the company have legitimate business operations in the foreign country?

Is that the same as the GILTI tax stuff I keep hearing about with foreign corporations? I thought that made foreign corps less attractive after the 2017 tax law changes.

Will this work if I'm not making a payment? I don't think I'll owe anything, but still need the extension to get my paperwork together.

If you don't need to make a payment, then Direct Pay won't work for your situation. In that case, you should use one of the free filing options mentioned above - IRS Free File or one of the tax software programs. Since you don't think you'll owe, just be absolutely certain about that. If you end up owing even a small amount and didn't pay by the regular deadline, you'll face penalties and interest. Many people accidentally underestimate what they owe and get hit with unexpected charges.

This is really good advice. Is there a calculator or something to help estimate if you'll owe? I haven't really kept good records this year.

Thanks for the suggestion about adjusting my withholding going forward. Do you know how I would calculate how much extra to withhold to make up for this year's shortfall? And you're right about the state taxes - I need to check those too. I was so shocked by the federal issue that I didn't even think about that.

You can use the IRS Tax Withholding Estimator on their website - it lets you input how much has been withheld so far and will calculate what you need for the remaining paychecks. Just select that you want a bigger refund and it'll tell you what number to put on your W-4. For your state taxes, each state has different rules, but if they weren't withholding federal, there's a good chance they missed state too, especially if you're in a state that bases its withholding on the federal W-4 form.

This is a really good point! OP needs to check their employment status. My neighbor thought she was a regular employee but her company had her classified as a 1099 contractor (incorrectly) and wasn't withholding anything. Led to a huge tax bill and she had to file an SS-8 form with the IRS to get it sorted out.

I just checked my tax return copy and all my banking info looks correct. I've been using the same account for direct deposits from the IRS for the past 3 tax seasons without issues. The status on the Where's My Refund tool specifically says "refund approved" with the May 3 date, not that there are any problems with the deposit info. Is it possible they're just extra backed up this year? It seems weird that they'd approve it but then wait so long to actually send the money.

Yes, they are definitely more backed up this year than usual. I've been preparing taxes for family members for years, and I've noticed much longer processing times this season. The IRS has been dealing with staffing shortages and outdated computer systems. When they approve a refund but schedule it for weeks later, it's often because they're spreading out the payment processing to manage their workflow. Think of it as them putting you in a payment queue based on various factors including filing date, complexity, and even the amount of the refund.

I tried contacting the Taxpayer Advocate Service last month for a similar issue. Unfortunately, they're also extremely backed up and told me they're only taking the most severe hardship cases right now. They said unless I was facing immediate eviction or had medical treatments I couldn't receive without the money, they couldn't help with "routine" refund delays.

Thanks for this! Question - do you know if I need to keep all the receipts from the post office for shipping costs or can I just use the eBay records that show what I spent on shipping?

You can absolutely use the eBay records that show shipping costs! eBay keeps excellent records of all shipping labels purchased through their platform, and those records are sufficient documentation for the IRS. Just download your yearly selling record which includes all those shipping costs. For any shipping supplies or postage you purchased outside of eBay (like buying boxes or stamps separately), you should try to keep those receipts, but even a credit card statement showing purchases at office supply stores can serve as backup documentation.

I switched from TurboTax to FreeTaxUSA last year for my eBay business. TurboTax wanted to charge me $120+ for the self-employment version, while FreeTaxUSA was way cheaper and handled Schedule C just fine.