Week 5 here and honestly this community has been more helpful than the IRS website itself 😭 @Ryan Andre thanks for the Tuesday/Thursday info - that's literally the first concrete timeline I've heard anywhere. Going to try that taxr.ai thing @Lauren Zeb mentioned because the "where's my refund" tool has been useless. At least now I know I'm not alone in this waiting game!

Week 2 of test batch here and honestly feeling way better after reading this thread! @Ryan Andre that Tuesday/Thursday processing schedule is incredibly helpful - finally have actual dates to work with instead of just refreshing constantly. @Charlotte White your success story after 6 weeks gives me hope! Going to definitely check out that taxr.ai tool @Lauren Zeb mentioned since the regular WMR has been completely useless. Thanks everyone for sharing your experiences - makes this whole waiting process feel less isolating when you know others are going through the exact same thing 🙏

Quick tip - if you're filing just one or a few 1099-NECs, the IRS actually has a free online filing portal called the FIRE system (Filing Information Returns Electronically). You don't need fancy software if you only have a few to do. You'll need to register for an account first, which takes a little time to set up, but once you have it, filing is pretty straightforward. For real estate commissions specifically, I've done this several times without issues.

Just want to add one more important point that I learned the hard way - make sure you keep detailed records of when you sent the 1099-NEC to the brokerage and when you filed with the IRS. I had a situation where a brokerage claimed they never received their copy, and having proof of mailing saved me from potential penalty issues. Also, double-check that the brokerage's legal name on the 1099 exactly matches what's on their W9 form. Even small differences like "LLC" vs "L.L.C." or missing punctuation can cause processing delays or correction notices from the IRS. With a $74k commission, you definitely want everything to be perfect the first time around. One last thing - if this is your first time filing 1099s, consider doing a test run with the forms before the actual filing. Most software and even the IRS FIRE system let you preview everything before submitting, which can catch mistakes early.

I want to echo what others have said about the IRS being more reasonable than most people expect. I work as a tax preparer and see situations like yours regularly - you're definitely not alone. One thing I'd add to the excellent advice already given: consider filing your most recent year (2024) first, even if it's just an estimate. This shows the IRS you're making a good faith effort to get current, which can help when negotiating penalties for the older years. Also, don't underestimate the Fresh Start program. The IRS expanded it significantly in recent years, and it offers more flexible payment options and penalty relief than many people realize. An Enrolled Agent can help you navigate whether you qualify for any of these provisions. For gathering documents, your local library often has free access to tax software that can help you print transcripts of past tax information if you've filed before. The IRS also has a "Get Transcript" service online that can show what they have on file for you. The most important thing is that you're addressing this now while you're in a more stable place mentally and financially. That timing will actually work in your favor when dealing with the IRS.

I'm so glad you posted this - it takes real courage to face a situation like this head-on. I went through something similar after my mom passed away and I completely understand that overwhelming feeling of everything falling apart while basic responsibilities pile up. One thing that really helped me was breaking this down into smaller, less scary steps. Before you even think about penalties or payment plans, start with just gathering information. You can request wage and income transcripts directly from the IRS for all those years - they'll show you what income they have on file for you. This gives you a baseline to work from. For your DoorDash year, if you still have the app, check if there's any way to access your annual summary or earnings history. Many gig apps keep this data longer than you'd expect. The reality is that for many people in situations like yours, especially with lower incomes from retail and gig work, you may actually be owed refunds for some of those years rather than owing money. The earned income tax credit alone can result in substantial refunds even if you had little to no taxes withheld. Don't let the fear of the unknown keep you paralyzed. The IRS deals with situations like yours every day, and there are so many programs designed to help people get back on track. You've already done the hardest part by getting your life stable again - this is just paperwork that can be sorted out. You've got this. Take it one year at a time.

Don't overlook the liability aspects too! Being a partner potentially exposes you to more business liability than being just an employee, depending on how the partnership is structured. If it's a general partnership interest, you could have unlimited personal liability for the business's debts and legal issues. If it's a limited partnership interest, your liability is usually capped at your investment. Since you mentioned it's an LLC, you should have some liability protection, but make sure to understand exactly what your partnership agreement says about this. Also check if the company maintains proper liability insurance for partners.

One aspect that hasn't been fully covered is the potential impact on your Social Security benefits calculation. As an employee, your employer pays half of your Social Security taxes, but as a partner, you'll pay the full 15.3% self-employment tax on your earnings (though you can deduct half of it). However, this actually means more of your income will count toward your Social Security earnings record, which could result in higher future Social Security benefits when you retire. Also, regarding the 401(k) loss - while you'll lose access to any employer matching, a Solo 401(k) as a partner can actually allow you to contribute both as the "employee" (up to $23,000 for 2024, or $30,500 if over 50) AND as the "employer" (up to 25% of compensation), potentially letting you save much more for retirement than a traditional employer plan. The key is running the numbers for your specific situation. The immediate tax changes might look concerning, but the long-term wealth-building potential of ownership, combined with the tax advantages available to business owners, often makes it worthwhile.

Have any of you tried leasing instead of buying? My accountant recommended I lease my vehicle through my business instead of buying it personally and trying to deduct it. Apparently the IRS scrutiny is different and the paperwork is cleaner.

Great question! As someone who's navigated similar waters with my consulting business, I'd recommend being very careful about the "mobile advertising" angle. The IRS is pretty strict about what constitutes legitimate business use versus personal convenience. From my experience, the key is documentation. If you're serious about this approach, you'll need to: 1) Keep detailed mileage logs showing actual business trips (not just driving around town with a logo) 2) Track any client meetings, business errands, or other legitimate business use 3) Calculate the exact business-use percentage and only deduct that portion The advertising value alone (logo/decals) won't justify deducting the vehicle payments. However, if you're genuinely driving to supplier meetings, client locations, or scouting new rental markets, those miles could count as business use. One alternative to consider: instead of trying to deduct your personal vehicle, maybe purchase the vehicle through your business entity from the start. If it's going to be part of your luxury rental expansion anyway, structuring it as a business asset from day one eliminates the personal-use complications entirely. Just remember, the IRS looks closely at lifestyle purchases that might be disguised as business expenses, especially in the $50-75k range. Make sure your business use is genuine and well-documented.