Thanks for this advice! Would it help if I started paying a portion of the rent directly to the landlord instead of giving the money to my boyfriend? I'm worried that the Cash App transfers labeled "rent" might not be enough proof since the actual rent receipts are in his name.

That would definitely strengthen your case! If you can arrange to pay even a portion directly to the landlord, that creates a clearer paper trail. Ask the landlord if they can note your payment specifically in their records, even if the lease remains in your boyfriend's name. The Cash App transfers labeled "rent" are still useful evidence, especially if they show a consistent pattern that aligns with rent due dates. But direct payments to the landlord would be more compelling. Also, consider getting a simple written statement from your boyfriend acknowledging that your Cash App transfers are contributions toward household expenses - this adds another layer of documentation.

I used TurboTax last year with a similar HOH situation. It asks you the basic qualifying questions but doesn't really get into documentation issues. It'll let you file HOH if you say you meet the requirements, but doesn't help you prove it or explain the gray areas. You might want to consult with a tax pro if you're uncertain.

Thanks for sharing your experience. Did you have any issues after filing with TurboTax? Like did the IRS question your HOH status afterward or did everything go through okay?

Do you happen to know what the threshold is for 2025? I'm trying to plan ahead and figure out if I'll be close to that 22% bracket.

For 2025, the threshold between the 12% and 22% brackets for single filers is projected to be around $47,150 (up from about $44,725 in 2023). For married filing jointly, it's projected to be about $94,300. These are estimates based on inflation projections, and the IRS will announce the official numbers later this year. But they should be pretty close to these figures unless inflation changes dramatically.

While I agree the system favors the wealthy, that's not entirely accurate. The top 1% pays about 40% of all federal income taxes collected. The issue is more about proportional tax burden and the different treatment of earned income vs capital gains.

17 Is there a minimum amount you have to make before reporting? I thought there was some threshold where you don't need to bother reporting small side income?

3 Technically, all income is supposed to be reported regardless of amount. However, if you make $400 or more in self-employment income, you're required to file taxes on it because that's the threshold for paying self-employment taxes. Some people talk about a $600 threshold, but that's actually just the limit where payment platforms or clients are required to send you a 1099 form. Even if you don't receive a 1099, you're still supposed to report the income. The IRS has been cracking down on unreported income from online platforms, so better safe than sorry!

13 Do you know if this applies if you're selling through platforms like Etsy or eBay? I thought they handled the sales tax stuff automatically?

Do Acceptance Agents charge a lot? And would using one make the process faster? My main concern is the timeline since I have potential clients waiting for me to get all this paperwork sorted out.

Acceptance Agents typically charge between $50-$300 depending on the complexity of your situation and their location. Some offer additional services like reviewing your entire application package. Using an Acceptance Agent can potentially make the process faster because they help ensure your application is complete and correct the first time, reducing the chance of rejection and resubmission. They also eliminate the risk of your original documents getting lost in the mail. However, they don't actually speed up the IRS processing time - once your application reaches the IRS, it still goes through their standard processing queue. That said, a complete and accurate application will move through that queue without delays.

Unfortunately there's no online tracking system for ITIN applications like there is for tax refunds. You have to call the IRS ITIN department directly at 1-800-908-9982. Make sure you have your application confirmation if you received one, or at least the information about when and how you submitted it.

I hadn't thought about the backdoor Roth approach. Would that still work if my tax liability is already zero? And would I still need to worry about the documentation of foreign expenses if I go that route?

The backdoor Roth works regardless of your tax liability because you're making non-deductible contributions to a traditional IRA first, which doesn't require you to have tax liability. You'd report these non-deductible contributions on Form 8606. No need to worry about foreign expense documentation for this approach. You can take the full standard deduction, apply your FTCs to reduce your tax to zero (carrying forward any excess), and still do the backdoor Roth. The only documentation you need is for the FTCs themselves (foreign tax statements or equivalent), not itemized expenses.

FTCs can only be carried forward, not backward. You can carry them forward for up to 10 years, but you can't apply them to prior year returns unfortunately.