


Ask the community...
Has anyone here dealt with converting a farm property from an LLC back to individual ownership before a parent's passing? We did this with my grandfather's farm last year to ensure we got the stepped-up basis, but now I'm worried about potential gift tax implications since the LLC was originally in our names (the kids).
When we did something similar, our tax attorney advised us to dissolve the LLC and distribute the property back to my father (the original owner) more than a year before any anticipated sale. There were no gift tax issues since it was going back to the original owner, but we did have to file some special paperwork with the property transfer. It worked out well - when he passed, we got the full stepped-up basis and saved about 35% on taxes when we eventually sold.
Thanks, that's reassuring! Did you have to pay any transfer taxes or recording fees when moving the property back to your father's name? Our county has some hefty transfer taxes, and I'm trying to figure out if there are any exemptions for this kind of family transfer.
The missing LLC documentation is a red flag that needs immediate attention, especially with BOI reporting deadlines approaching. I'd recommend starting with your state's Secretary of State office - they should have the Articles of Organization on file that will show who signed as the organizer and initial members. For the stepped-up basis question, the key factor is who actually owns the LLC membership interests at the time of your father's death. If he retained ownership (making it a single-member LLC), the property gets stepped-up basis. If you kids already own the LLC, no step-up occurs since you technically already own the property. Given the Medicaid planning aspect, I suspect the LLC ownership was likely transferred to you children to protect the asset, which would unfortunately eliminate the stepped-up basis benefit. However, if your father retained even a small percentage of ownership, that portion would qualify for step-up. You might want to consider having the LLC dissolve and distribute the property back to your father if he's still healthy and the goal is to maximize the stepped-up basis for your family. Just be mindful of the Medicaid lookback period implications that others have mentioned.
This is really helpful advice, especially about checking with the Secretary of State office first. I'm new to dealing with estate planning issues, but this whole thread has been eye-opening about how complex these LLC arrangements can get. One thing I'm wondering - if we do find out that my father retained some ownership percentage, is there a way to restructure things now to maximize the stepped-up basis without running into Medicaid issues? It sounds like there might be a narrow window to make changes, but I'm not sure what the best approach would be for someone just starting to understand these rules. Also, does anyone know if the BOI reporting requirements might actually help us figure out the current ownership structure, or is that something we need to resolve before we can even file the BOI report?
Don't stress too much! I work with a lot of freelancers and this happens more than you'd think. Here's what I tell them: always report your REAL income, not what's on an incorrect form. The IRS computers mainly flag when reported income is LOWER than what's on forms. When you report MORE, it rarely triggers issues. Think about it - the IRS is happy when you pay taxes on more income! Keep solid records, but don't lose sleep over this. The startup's mistake shouldn't become your problem.
So what exactly should we put on Schedule C in this situation? Do we list the 1099 amount and then add the additional income somewhere else, or just put the total correct amount?
On Schedule C, you just report the total correct amount of income you actually received. Don't try to split it between what's on the 1099 and what's missing - just put the full, accurate total on the appropriate income line. The IRS matching system will see that you reported MORE than what's on the 1099, which typically doesn't trigger any automated notices. If by some chance there are questions later, your documentation showing the actual payments received will support the higher amount you reported. Keep it simple - accurate total income on Schedule C, solid records in your files, and you're good to go!
I went through this exact same situation two years ago with a small marketing agency that basically disappeared after sending me an incorrect 1099. Here's what I learned: First, you're absolutely right to report the actual amount you received - that's what the IRS expects. I reported the correct (higher) income on my Schedule C and kept detailed records of all my payments, invoices, and attempts to contact the company. The key thing that gave me peace of mind was creating a simple one-page summary document that I kept with my tax records. It listed: - The incorrect 1099 amount vs. actual income received - Dates and methods of all my attempts to get it corrected - A brief explanation that the company became unresponsive I never needed to submit this with my return, but having it organized made me feel much more confident about my filing. The IRS never questioned anything because I reported MORE income than what was on their forms. Your bank deposits and invoices are solid evidence - you're in good shape. Don't let their poor record-keeping create stress for you when you're doing everything correctly!
This is incredibly helpful - thank you for sharing your experience! I like the idea of creating that one-page summary document. It sounds like having everything organized in one place would make me feel much more confident about the whole situation, even if I never have to actually use it. Did you find that having those detailed records made you less anxious about potential future questions from the IRS? I keep worrying that somehow this discrepancy will come back to haunt me years later, but it sounds like when you're reporting MORE income rather than less, it's really not something to lose sleep over.
I've dealt with this exact scenario multiple times as a tax preparer. Here's what you need to know about FreeTaxUSA and ISO reporting: For your $2,300 spread, you're likely correct that your AMT will be $0 due to the exemption amounts for 2024 ($85,700 for single filers, $133,300 for married filing jointly). However, you still need to properly report the ISO adjustment. In FreeTaxUSA, the ISO spread should be entered under the "Federal" section ā "Deductions & Credits" ā "Other Taxes" ā look for "Alternative Minimum Tax (AMT)" subsection. If you don't see this initially, make sure you've indicated stock option activity in the interview questions as others mentioned. The key point everyone seems to be missing: even if your current AMT is $0, you're creating an AMT credit that carries forward. This credit becomes valuable when you eventually sell the ISO shares, as it reduces your regular tax liability dollar-for-dollar up to the amount of AMT you would have paid. For record-keeping, maintain detailed records of: - Exercise date and number of shares - Exercise price per share - Fair market value on exercise date - AMT adjustment amount ($2,300 in your case) - Any AMT paid (likely $0 for you) This information is crucial for calculating your adjusted cost basis when you sell, which affects whether the sale generates ordinary income or capital gains treatment.
This is incredibly helpful, thank you! I had no idea about the AMT credit carryforward aspect. So even though I'm not paying AMT now with my small spread, I'm still building up a credit that I can use when I eventually sell these shares? Can you clarify what you mean by "adjusted cost basis"? Is this different from just using the exercise price as my basis? And when you say it affects ordinary income vs capital gains treatment, are you referring to the disqualifying vs qualifying disposition rules for ISOs? I want to make sure I understand this correctly since it sounds like the tax implications when I sell could be quite different depending on how I handle this now.
Exactly right! Even with $0 current AMT, you're building AMT credit. Think of it as a prepayment - the IRS recognizes you'll pay tax later when you sell. For basis: Your regular tax basis is the exercise price you paid. But for AMT purposes, your basis is exercise price PLUS the spread amount ($2,300). This higher AMT basis reduces future AMT income when you sell. The AMT credit bridges this gap. When you sell and calculate both regular and AMT tax, if your regular tax exceeds AMT tax (which usually happens), you can use prior AMT credits to reduce your regular tax bill. Regarding ordinary vs capital gains: That's about holding periods for ISOs. Hold >2 years from grant AND >1 year from exercise = qualifying disposition (capital gains rates). Sell earlier = disqualifying disposition (ordinary income rates on the spread, capital gains on any additional appreciation). The AMT credit applies regardless of which type of disposition you have - it's a separate calculation that runs parallel to determine your final tax liability. Bottom line: Report that $2,300 spread now even with $0 AMT due. Your future self will thank you when you sell those shares and can use the credit!
Just wanted to add my experience as someone who went through this exact situation last year. I had a $2,800 ISO spread and was also using FreeTaxUSA, wondering if I needed Form 6251. After reading through all these helpful responses, I ended up doing what several people suggested - I manually calculated Form 6251 to confirm my AMT was $0, then made sure to enter the ISO spread amount in FreeTaxUSA under the AMT section. The key thing I learned (and wish I'd known earlier) is that even though my current AMT was $0, I was still creating valuable AMT credits for the future. When I sold half my ISO shares this year after holding them for the required periods, those AMT credits saved me about $1,200 in regular taxes. For anyone in a similar situation: don't skip reporting the ISO spread just because you think your AMT will be zero. The credit tracking is worth it, and FreeTaxUSA does handle it properly once you find the right section. Also, definitely keep detailed records of everything - exercise dates, FMVs, spreads, etc. You'll need all of this when you eventually sell. The whole ISO/AMT system is confusing, but taking the time to understand it now will pay off significantly when you sell those shares down the road.
This is exactly the kind of real-world experience I was hoping to hear about! Thank you for sharing how the AMT credits actually worked out when you sold your shares. That $1,200 savings really puts it in perspective - definitely worth the effort to properly report the ISO spread now even with $0 current AMT. Your point about keeping detailed records resonates with me too. I've been somewhat lazy about tracking all the specifics, but seeing how it paid off for you when you sold makes me realize I need to get more organized with my ISO documentation. One quick question: when you sold your shares after the required holding periods, did you have to do any special calculations to claim those AMT credits, or did FreeTaxUSA handle that automatically once you entered the sale information?
Just joined this community and wow, what a mess TurboTax has created with their refund advance tracking! Reading through everyone's experiences, it's clear this is a widespread issue that shouldn't exist. I'm dealing with the same problem right now - filed two weeks ago with the 5-day advance option and have been checking my regular bank account daily like an idiot. After seeing NeonNinja's advice about Green Dot, I downloaded their app and sure enough, my advance has been sitting there since last Wednesday! It's honestly infuriating that TurboTax doesn't make this process transparent. They take a fee for "convenience" but then make you hunt through multiple apps and banking partners to find your own money. The fact that they're apparently using different partners (Green Dot, Credit Karma Money, etc.) without clearly communicating which one applies to your situation is just poor customer service. Thanks to everyone who shared their experiences here - this thread solved in 10 minutes what TurboTax's own support couldn't clarify. Definitely going the direct deposit route next year!
Malia, welcome to the community and I'm so glad you found your money! Your experience really highlights how broken this system is. I'm also new here and just went through the exact same runaround. It's mind-blowing that we're all having to crowdsource solutions for something that should be straightforward. The fact that TurboTax charges fees for this "service" while making us detective work to access our own funds is beyond frustrating. I ended up calling their support line (after a 2-hour wait) and the rep seemed genuinely confused about which banking partner my advance went through. That tells you everything you need to know about how poorly this is managed internally. Thank you and everyone else for sharing your stories - it's clear this community is providing better support than TurboTax themselves!
As another newcomer who just went through this exact nightmare, I wanted to share what finally worked for me. After reading through all these helpful comments, I checked my email more thoroughly and found not one, but THREE different emails from TurboTax about my refund advance - one initial confirmation, one from Green Dot with setup instructions, and a third one that got buried in my promotions tab with the actual account details. The Green Dot app route that NeonNinja mentioned saved me too! My advance had been sitting there for almost a week while I was frantically checking my regular bank account. What's really frustrating is that TurboTax's own "Refund Status" page just showed "processing" with no mention of where to actually look for the funds. It's clear from everyone's experiences that this isn't just user error - TurboTax has genuinely created a confusing system with multiple banking partners and poor communication. I'm definitely joining the "direct deposit only" club next year. Thanks to this community for being more helpful than TurboTax's actual customer service!
Xan Dae
I completely understand your panic about this situation - I work as a tax preparer and see this exact scenario with online gambling platforms multiple times every tax season. The good news is you're absolutely NOT stuck paying taxes on $68,000 you didn't actually win. The W2-G is misleading because it only reports individual winning transactions over the threshold ($1,200+ for slots), not your actual net gambling results. Since you mentioned being down money overall with DraftKings for the year, you should be able to offset that reported income with your documented losses. Here's your action plan: **Immediate steps:** - Request your complete annual win/loss statement from DraftKings showing ALL activity for the tax year - This will likely show you had a net loss, which is what actually matters for taxes **Filing process:** - Report the full $68,000 on Schedule 1, Line 8b as required - Deduct your gambling losses on Schedule A (up to the amount of winnings) - Compare itemizing vs. standard deduction to see which saves more money **Key point:** You can only claim gambling losses if you itemize deductions, but with $68,000 in reported winnings to offset, itemizing will almost certainly save you thousands even if you lose other deductions. Keep all your DraftKings documentation - their annual statements are comprehensive and IRS-acceptable. You haven't financially ruined yourself; you just need to navigate the somewhat counterintuitive way gambling taxes work. The system does protect people in your exact situation when you follow the proper procedures.
0 coins
Eva St. Cyr
ā¢This is such helpful professional insight, thank you! As someone who's completely new to dealing with gambling taxes, I really appreciate having a tax preparer explain this so clearly. I had no idea that the W2-G only reports individual winning sessions rather than net results - that explains why I was so confused and panicked when I saw that $68,000 figure. It seemed impossible that I could owe taxes on money I never actually received. I'm definitely going to request that annual statement from DraftKings right away. Based on what everyone here is saying, it sounds like it should clearly show that I had a net loss for the year, which would offset most or all of that reported income. One question about the itemizing decision - when you help clients with similar situations, are there any other factors besides just comparing the total deduction amounts that I should consider? Like are there any long-term implications of itemizing versus taking the standard deduction that might affect future tax years? @Xan Dae Really grateful for your professional perspective on this. It s'giving me so much more confidence that I can handle this properly without making costly mistakes.
0 coins
Yara Khoury
I understand the overwhelming stress you're feeling about this situation - getting a massive W2-G when you actually lost money overall is one of the most anxiety-inducing tax scenarios out there. But I want to reassure you that you have NOT financially ruined yourself. The system seems backwards, but it does work when you understand the process. That $68,000 W2-G represents individual winning spins that hit the reporting threshold, not your actual profit. Since you mentioned losing money overall with DraftKings, you should be able to offset most or all of that reported income. Here's what you need to focus on right now: **Get your documentation immediately:** Request DraftKings' annual win/loss statement through your account (usually under "Responsible Gaming" or "Tax Documents"). This will show your true net position for the entire year. **Understand the filing process:** You'll report the $68,000 on Schedule 1 as required, but then deduct your actual losses on Schedule A up to that amount. Yes, this means you'll need to itemize, but with losses potentially offsetting $68k in income, itemizing will almost certainly save you thousands. **Don't panic about audits:** With proper documentation from DraftKings showing your actual gambling activity and results, you're well-protected if questioned. The most important thing to remember is that the IRS isn't trying to tax you on money you didn't actually win - the reporting system is just clunky. Once you get that annual statement showing your net loss position, you'll feel so much better about this whole situation.
0 coins