This has been such an educational thread! As someone who's considering selling some investment property in the next year or two, I had no idea about all these potential issues with 1099-S forms and title company procedures. Reading through everyone's experiences - from address mix-ups to processing delays to the various backup options - has given me a much better understanding of what to expect and prepare for. I'm definitely going to create a checklist based on all the advice shared here: verify mailing address at closing, ask about 1099-S timing, keep all settlement documents organized, and know that services like taxr.ai and Claimyr exist if needed. It's also really reassuring to learn about the IRS "reasonable cause" provision and that you can file accurately using settlement statements if the official form is delayed. Thanks to everyone who shared their real-world experiences and especially to the tax professionals who provided additional context. This is exactly the kind of practical, community-driven advice that makes navigating complex tax situations so much less intimidating!

This thread has been absolutely invaluable! I'm currently dealing with a similar issue - sold some investment property last year and haven't received my 1099-S yet. Reading through all these experiences has been both reassuring and educational. What strikes me most is how common these documentation issues seem to be, yet how many viable solutions exist. From simply calling the title company about address mix-ups, to using services like taxr.ai for generating substitute forms, to Claimyr for actually getting through to the IRS - it's clear there are multiple paths to resolve these situations. The professional insights about the "reasonable cause" provision and being able to file accurately using settlement statements are particularly valuable. It's comforting to know that the IRS recognizes good faith efforts and that you're not stuck if one document goes missing. I'm going to start by calling my title company tomorrow to check on the status, but now I feel much more confident knowing I have backup options if needed. Thanks to everyone who shared their experiences - this community really shines when it comes to helping people navigate these tricky tax situations!

Just want to add a quick tip that saved me a lot of headaches - download a mileage tracking app BEFORE your first dash! I started DoorDash last summer and forgot to track my miles for the first month. Trying to recreate that data from memory and old delivery screenshots was a nightmare. Also, consider doing a "test week" where you carefully track all your expenses (gas, time, wear on your car) versus earnings to make sure DoorDash will actually be profitable for your car fund goal. In my area, after factoring in gas prices and the extra maintenance my car needed, I was making less per hour than I initially calculated. Still worth it for the flexibility, but good to know the real numbers upfront. One last thing - if you're planning to dash during dinner rush or weekends, those tend to be the most profitable times but also when you'll put the most miles on your car. Just something to keep in mind for your savings timeline!

Just wanted to chime in with something that might help with your quarterly tax situation! Since you mentioned you're already rebuilding your emergency fund and investing from your regular job, you might actually be in a good position to avoid quarterly payments altogether. If your current W-2 withholding covers at least 100% of last year's total tax liability (or 110% if you made over $150k), you won't owe penalties even if you don't make quarterly payments on your DoorDash income. You'd just pay the extra amount when you file your return in April. This could simplify things for you - instead of trying to estimate quarterly payments as a new dasher, you could just set aside money in that separate car fund account and settle up at tax time. Just make sure you're disciplined about saving that 25-30% that others mentioned! The other option, like Connor mentioned, is bumping up your W-4 withholding at your main job. Might be worth running the numbers both ways to see what works better for your cash flow and car saving timeline.

As a quick aside, make sure you're still checking the "Not required to file Schedules L, M-1 and M-2" box on page 1 of your 1065 if you qualify for the exemption, even if you're filling them out for your own records. I've seen the IRS send notices when this box isn't checked but the schedules are included.

I've been dealing with this same issue for my LLC partnership and found a simpler approach that might help. Since you're exempt from filing these schedules, consider this workflow: 1. Complete Schedule M-1 as normal (sounds like yours is working fine) 2. For Schedule L, maintain your current book capital accounting method 3. Use the override function in H&R Block for Line 21 to match your books 4. Complete Schedule M-2 separately just to see the tax basis capital calculation This way you get the benefit of seeing both perspectives - your book capital (which is what you use to manage the business) and the tax basis capital (which shows what the IRS methodology would be). You don't need to force them to match since you're not filing. I actually find this dual approach more informative than trying to reconcile everything. It shows me how distributions and income allocations would be treated differently under tax rules versus my business accounting, which helps with planning future transactions. Just make sure to check the exemption box on page 1 of the 1065 as others mentioned!

I went through this exact situation two years ago when my wife was a surrogate. After consulting with a tax attorney who specializes in reproductive law, we learned that the IRS generally treats surrogacy compensation as taxable income, but the classification (self-employment vs. other income) can make a huge difference in your tax liability. The key factors that helped us determine the proper reporting were: 1) Whether this was a one-time arrangement or part of an ongoing business, 2) How the contract was structured, and 3) The level of control the intended parents had over the process. In our case, we reported it as "other income" on Schedule 1 rather than self-employment income, which saved us thousands in self-employment taxes. We documented everything meticulously - separating actual compensation from medical expense reimbursements, which aren't taxable if properly documented. Don't let the agency's informal advice guide your tax decisions. The $42,000 you mentioned is significant enough that the IRS would likely notice if it's not reported, especially if it was paid via check or bank transfer. Better to be conservative and report it properly than face potential penalties later. I'd strongly recommend consulting with a CPA who has experience with surrogacy cases - it's worth the consultation fee for peace of mind on something this substantial.

I'm a tax professional who has worked with several surrogacy cases, and I want to emphasize that proper documentation is absolutely critical here. The IRS will want to see clear separation between taxable compensation and non-taxable reimbursements. For documentation, you should maintain: 1) The original surrogacy contract showing payment breakdown, 2) Bank statements for all payments received, 3) Receipts for any unreimbursed expenses you plan to deduct, 4) Medical records showing expense reimbursements were for actual costs incurred, and 5) A detailed spreadsheet tracking each payment and its purpose. The $42,000 compensation amount puts you well above reporting thresholds, so this income will definitely need to be reported. Based on what you've described - one-time arrangement through an agency - reporting as "other income" on Schedule 1, Line 8 rather than Schedule C self-employment income is likely the correct approach, which would save you significant self-employment taxes. However, given the complexity and financial impact, I'd strongly recommend getting a consultation with a CPA experienced in reproductive law cases. The consultation fee will be minimal compared to potential tax savings or avoiding penalties from incorrect reporting.

I just want to echo what others have said - you're definitely not in trouble! I had almost the identical situation last year with a 2020 return I filed super late. The "Available for pickup" status had me panicking too, but it turns out that's completely normal for IRS PO Boxes. One thing I learned that might help: if your brother is expecting a refund, he can actually check the IRS "Where's My Refund" tool online after about 4-6 weeks from when you mailed it. You'll need his SSN, filing status, and the exact refund amount from the return. Even though it was mailed (not e-filed), it will eventually show up in that system once they process it. Also, since you mentioned he had a small business that closed in 2022, make sure you kept copies of everything you sent. The IRS sometimes requests additional documentation for final business returns, especially if there were any assets that were sold or depreciated equipment involved. Having everything organized will save you headaches later if they send any follow-up letters. Don't resend anything - just be patient. The March 12th postmark protects you from any late filing penalties, and that's what really matters here!

Just to add another perspective - I work as a tax preparer and deal with mailed returns regularly. What you're experiencing is completely normal and happens all the time with IRS PO Box deliveries. The "Available for pickup" status actually confirms that USPS successfully delivered your return to the correct IRS processing facility. One thing I always tell my clients is to create a simple filing timeline for themselves. Mark down March 12th as your postmark date (which protects you from penalties), then add 6-8 weeks for basic processing or 10-12 weeks for business returns. That puts you at roughly mid-to-late May for when you should start seeing updates in the IRS systems. Since this involves a closed business from 2021, the IRS will likely take extra time to verify the final income figures and make sure all business taxes were properly calculated. This is routine for final business returns - they're not targeting you specifically, they just have additional verification steps for business closures. The most important thing is that you've met the filing deadline with your March postmark. Everything else is just waiting for the bureaucratic wheels to turn. Keep that USPS tracking info handy as your proof of timely filing, and try not to stress about the processing delays - they're unfortunately just part of dealing with paper returns these days.