As someone who went through a similar situation last year, I can't stress enough how important it is to get this clarified immediately. My partner and I were also told by a tax preparer that we could "basically file together" and it turned out they meant we should coordinate our filings to maximize deductions (like one taking all charitable contributions, the other taking all business expenses), not actually file a joint return. The distinction is huge - coordinating your separate returns is smart tax planning, but filing a joint return while unmarried is illegal. I ended up calling the IRS taxpayer advocate service (877-777-4778) to get official clarification, and they were very clear about the rules. Given that you mentioned you're getting married in December, you might want to consider whether it makes sense to move up your wedding date if the tax savings are substantial. Being married by December 31st would allow you to file jointly for the entire 2024 tax year when you file next year. But for your current 2023 taxes, you definitely need to file as unmarried individuals. Please don't risk it - the penalties and interest on incorrect filings can be brutal, and it's not worth the stress of wondering if the IRS will catch it later.

Just wanted to add another perspective here as someone who's dealt with tax complications before. The fact that multiple tax professionals and IRS representatives have confirmed that unmarried couples cannot file jointly should definitely give you pause about your advisor's recommendation. One thing that hasn't been mentioned yet is that if you did file incorrectly and the IRS discovered it later, you'd not only face penalties and interest, but you'd also have to file amended returns for each incorrect year. This process can be time-consuming and expensive, especially if you need professional help to fix everything. Since you mentioned you're getting married in December, here's a thought: if the tax savings from joint filing would be significant, you might want to run the numbers on what a small courthouse wedding before December 31st would save you versus waiting until your planned wedding. Sometimes the math works out in favor of having a legal ceremony earlier and then having your celebration later. But for your current 2023 taxes that you extended, you absolutely need to file as single individuals. Don't let the potential savings tempt you into taking a risk that could cost you much more in the long run. The IRS has gotten much better at cross-referencing data, so the chances of this going unnoticed are pretty slim.

Watch your mailbox carefully. Unlike regular returns, amended returns ALWAYS come as paper checks. This is different from how they handle normal returns, and unlike state amended returns (some states do direct deposit for amendments). I've had two amended returns in the past three years, and both came as paper checks despite having direct deposit info on file. The second one actually got lost in the mail and I had to request a trace, which added another 6 weeks to the process.

Just wanted to chime in as someone who works in tax prep - everyone here is absolutely right about paper checks only for amended returns. The IRS systems for processing 1040X forms are completely separate from their regular return processing, which is why they can't do direct deposit for amendments. One thing I'd add that I don't think anyone mentioned yet: make sure the address on your 1040X matches exactly what the IRS has on file, including any apartment numbers or suite numbers. I've seen clients have checks delayed or returned because of small address discrepancies. You can verify your address with the IRS by looking at your most recent tax transcript or calling their automated line at 1-800-829-1040. Also, if you move between filing your 1040X and receiving your refund, you'll need to file Form 8822 (Change of Address) with the IRS. Regular mail forwarding through USPS doesn't always work for IRS checks since they're often sent via certified or registered mail. Hope this helps and good luck with your refund!

I'm in the same boat with Lyft too! I just use the annual summary from the driver portal for my taxes. My tax guy said it's totally fine to use that instead of an official 1099. Just make sure you're tracking your mileage with an app throughout the year cause that's where the big deductions are!

This is such a frustrating situation that so many gig workers are dealing with! I had the same issue with Uber last year - made about $8,500 and got absolutely nothing from them while other platforms sent forms for much smaller amounts. After reading through all these comments, I think the key takeaway is that while it's annoying, we're not actually missing out on anything tax-wise. The IRS cares about accurate income reporting, not whether you have a piece of paper. I ended up using my Uber annual summary along with my bank deposit records to file my taxes. What really helped me was setting up a separate checking account just for gig work deposits. That way I had a clean paper trail of all my earnings throughout the year, regardless of which companies sent forms and which didn't. Makes tax time way less stressful when you're not scrambling to piece together income from different apps with different reporting methods. For anyone still dealing with this - don't waste hours on the phone with Uber support like I did. Just download your annual summary, track your mileage religiously, and move on with filing your taxes!

I just wanted to add one more consideration that I haven't seen mentioned yet - the timing of tax obligations. With W-2 income, your employer handles all the withholding throughout the year, so you're essentially paying taxes as you go. If you route this through your LLC, you'd be responsible for making quarterly estimated tax payments on that $65k. Miss those payments or underestimate them, and you could face underpayment penalties from the IRS on top of everything else. Given that this bonus is coming at year-end, you'd likely owe a substantial amount in taxes by January 15th (the Q4 estimated payment deadline). That's a big cash flow hit right after the holidays, versus having the taxes already withheld from your bonus when you receive it. Just another reason why the straightforward W-2 approach is usually the way to go, especially for large one-time payments like bonuses. The tax system is really designed around the assumption that employee compensation flows through payroll, and trying to work around that creates more problems than it solves.

I'm really glad I found this thread before making what would have been a serious mistake! I was in almost the exact same boat - getting conflicting advice about routing my bonus through my LLC and thinking it sounded like a great way to save on taxes. Reading through everyone's experiences and explanations has made it crystal clear that this approach would actually cost me MORE money, not less. The breakdown of how self-employment taxes work (15.3% vs 7.65%) was particularly eye-opening. I had no idea I'd be paying double the employment taxes! Beyond the tax implications, the points about IRS scrutiny for employee misclassification and the potential impact on future Social Security benefits really sealed the deal for me. It's just not worth the risk for what turns out to be negative savings anyway. I'm definitely going to stick with taking my bonus as regular W-2 income and focus on maxing out my 401(k) contributions instead. It might not feel as "clever" as finding some loophole, but it's clearly the smart, safe approach that actually provides legitimate tax benefits. Thanks to everyone who shared their real-world experiences and expertise - you probably saved me thousands in penalties and headaches!

Has anyone used TurboTax for reporting room rentals in their primary residence? I'm in a similar situation and wondering if I need to pay for their more expensive version or if the basic one will handle this correctly.

Just wanted to share my experience as someone who's been renting out rooms in my house for about 3 years now. One thing I learned the hard way is to keep extremely detailed records of everything - not just the big renovations like your bathroom project, but also all the smaller maintenance items throughout the year. Things like replacing faucets, fixing leaky pipes, repainting rooms between tenants, etc. can really add up and many of these qualify as immediate repairs rather than improvements. For your $22k bathroom renovation, definitely work with a tax professional if you can afford it. The distinction between repairs and improvements can save you thousands. For example, if you're replacing a broken toilet, that's a repair. But if you're upgrading to a fancy new toilet when the old one worked fine, that's an improvement. Sometimes a single project can include both elements. Also, don't forget about the home office deduction if you use part of your house exclusively for managing your rental business - storing supplies, doing paperwork, meeting with potential tenants, etc. It's another deduction that many accidental landlords miss!