Something no one has mentioned yet - have you considered using a Self-Directed IRA LLC (sometimes called a checkbook IRA) instead of ROBS? It might be better suited for real estate investments and doesn't require setting up a C-corp or dealing with the active business requirement. The downside is you can't personally benefit from the properties or be involved in day-to-day management, but for pure investment purposes it might be a cleaner structure. Just make sure you understand prohibited transaction rules because they're strictly enforced.

I've been following this discussion closely as I'm considering a similar structure. One thing I haven't seen mentioned is the potential impact of the Corporate Transparency Act (CTA) on ROBS structures. Since your C-corp would likely be considered a "reporting company" under the new beneficial ownership reporting requirements, you'll need to file FinCEN reports disclosing ownership information. This adds another layer of compliance but shouldn't affect the tax treatment of your ROBS. Also, regarding the LLC structure you mentioned - make sure you understand how the K-1 income will be treated at the C-corp level. Since C-corps don't get pass-through treatment, the rental income will be subject to corporate tax rates, and if you later want to access those funds personally, you'll face potential double taxation through dividends. Have you considered whether the rental income strategy makes sense given that corporate tax treatment, or would you be better off with a structure that allows pass-through taxation?

Does anyone know if having unfiled taxes will affect getting approved for an apartment? I'm in the same boat (didn't file 2021) and I'm trying to move next month. Worried this might show up on background checks...

Don't stress too much about this! With an income of $19,500 in 2021, you're likely in a pretty good position. Given that amount, you probably had taxes withheld from your paychecks throughout the year, which means there's a decent chance you're actually owed a refund rather than owing money. Here's what I'd recommend: gather all your W-2s and 1099s from 2021, then use tax software that handles prior year returns or consider working with a tax professional who can walk you through the process. The most important thing is to file as soon as possible - not because you're in terrible trouble, but because if you are owed money, you want to claim it before the April 2025 deadline. If it turns out you do owe a small amount, the IRS offers payment plans and is generally reasonable to work with, especially for first-time late filers. The anxiety you're feeling is totally normal, but the reality is usually much less scary than what we build up in our heads. You've got this!

This has been such an informative discussion! As someone who's been completely overwhelmed trying to understand what 2026 will bring, reading through all these perspectives has really helped clarify the scope of changes we're facing. I'm particularly struck by how many different moving parts there are - it's not just about tax rates going up, but also the standard deduction changes, AMT exemption reversions, QBI deduction expiration, Child Tax Credit reductions, and the return of various itemized deductions. The interactions between all these changes seem like they could create very different outcomes depending on your specific situation. What's becoming clear to me is that there's no one-size-fits-all answer to how these changes will affect people. Someone with high state taxes might actually come out ahead with unlimited SALT deductions despite higher rates, while a family with kids in a low-tax state could face a significant increase from losing the expanded Child Tax Credit and standard deduction. The uncertainty about Congressional action makes it even more challenging. It sounds like the smart approach is to prepare for multiple scenarios rather than betting on any specific outcome. I'm definitely going to start running some numbers for my own situation and probably consult with a tax professional before making any major financial moves in 2025. Thanks to everyone who shared their insights and experiences - this kind of real-world discussion is so much more helpful than trying to parse through dense policy articles alone!

As a newcomer to this community, I have to say this thread has been incredibly educational! I've been dreading 2026 without really understanding why, but seeing all the specifics laid out here really helps put things in perspective. What's particularly eye-opening is learning about provisions I had never even heard of, like the QBI deduction for self-employed folks and the AMT exemption changes. I always thought the 2026 "tax cliff" was just about rates going up, but it's clearly much more complex than that. The tools and services mentioned throughout this discussion seem really valuable - I had no idea there were resources available to help model these different scenarios or navigate the IRS maze more efficiently. As someone who typically just uses basic tax software and hopes for the best, it sounds like 2026 might be the year I need to step up my tax planning game. I'm especially grateful for the professional perspectives shared here. It's reassuring to know that even tax preparers find these interactions complex - makes me feel less foolish for being confused by it all! One question I have after reading everything: for someone like me who's relatively new to serious tax planning, what would be the most important first step to take in 2025 to prepare for these changes? Should I focus on understanding my current situation first, or jump straight into scenario planning for 2026?

I was in your exact shoes last year and completely understand the anxiety! I filed my Section 475(f) election with my 2023 return and spent months worrying about whether it was properly processed. Here's what I learned after going through this: the IRS doesn't send confirmation notices for MTM elections, which is incredibly frustrating but apparently normal. Since your return was accepted through ID.me, that's actually a good sign - it means they processed your return including any attached statements. A few practical tips that helped me: 1. Keep detailed records of everything - your original election statement, certified mail receipts, screenshots of your accepted return status 2. Start implementing MTM accounting immediately for 2024 - track all positions daily and mark them to market on December 31st 3. Prepare to file Schedule C for your trading activity instead of Schedule D The reality is that unless the IRS specifically rejects your election (which they would notify you about), it's considered valid. I know it's nerve-wracking not having definitive confirmation, but based on what you've described, your election should be in effect. I'm now filing my second year under MTM status and it's become much less stressful once you get into the routine. The key is just staying organized with your position tracking and treating your trading as a business from day one.

I went through this exact same anxiety with my Section 475(f) election! Filed it with my 2023 return and spent weeks obsessing over whether it was properly processed since there's no confirmation system. What finally put my mind at ease was understanding that the IRS operates on a "deemed approved unless specifically rejected" basis for these elections. Since your return was accepted and you haven't received any rejection notices, your MTM election is almost certainly valid and in effect. Here's what I wish someone had told me earlier: start implementing MTM accounting practices immediately for 2024. Don't wait for confirmation that will never come. Track your positions daily, maintain detailed records of market values, and prepare to report everything as ordinary business income on Schedule C rather than capital gains. The transition from worrying about election status to actually implementing MTM has been much smoother than I expected. Yes, it requires more detailed record-keeping than traditional capital gains reporting, but the tax benefits (especially full deductibility of losses against ordinary income) make it worthwhile. Keep your certified mail receipt, your election statement copy, and screenshots of your accepted return status. That paper trail is your confirmation. The IRS may not send you a gold star, but your election is valid if properly filed and not rejected. You've got this - the hardest part (making the election and getting through the uncertainty) is behind you!

Has anyone dealt with vendors who refuse to provide W9s? We have a few local businesses that get suspicious when we ask, even though we're just trying to follow the rules.

I've been following this thread and wanted to share our experience as a mid-sized nonprofit that went through similar W9 confusion last year. We initially had our finance team requesting W9s for every vendor too, but quickly realized it was creating more problems than it solved. What worked for us was implementing a two-tier system: automatic W9 collection for any vendor we expect to pay over $300 annually (giving us a buffer), and quarterly reviews of all vendor payments to catch anyone approaching $600. We use a simple Excel tracker that flags vendors at $400 and $550 thresholds. The key insight was that most of our vendor relationships are either very small (under $100 annually) or clearly going to exceed $600 - there aren't many vendors in that middle ground where tracking becomes tricky. For the 5-10 vendors per year that unexpectedly approach $600, we just request W9s when we notice during our quarterly reviews. This approach reduced our W9 collection efforts by about 80% while maintaining full compliance. Our program staff can focus on service delivery instead of chasing gas stations for tax forms!