This thread has been incredibly helpful - thank you all for sharing your real experiences! I'm in a similar position with a property sale and have been getting pitched on DSTs left and right. What really stands out to me from reading through everyone's comments is that the legitimate DST arrangements seem to require giving up immediate access to most of your proceeds (like Maya's 30% upfront structure), while the sketchy ones promise you can have your cake and eat it too (90%+ upfront with full tax deferral). I think I'm going to follow Emma's advice and run a proper financial analysis including all fees before getting swept up in the tax deferral excitement. The 3.5% upfront fee that Ava mentioned would cost me over $50K on my transaction - that's a lot of capital gains tax I could pay instead! Has anyone here worked with a fee-only financial planner (not someone selling DSTs) to evaluate whether these arrangements actually make sense? I'm thinking an independent analysis might be worth the cost before I commit to anything.

This entire discussion has been eye-opening! As someone who works in tax preparation, I see clients getting pitched on DSTs constantly, and the sales tactics are often quite aggressive. What concerns me most is that many promoters are targeting people who aren't sophisticated enough to understand the risks. A few red flags I tell my clients to watch for: 1) Any promoter who guarantees the arrangement will never be challenged by the IRS, 2) Promises of getting 80%+ of proceeds upfront while deferring all taxes, 3) High-pressure tactics claiming "this opportunity won't last," and 4) Reluctance to provide detailed documentation for independent review. The legitimate DST arrangements I've seen typically involve substantial genuine deferrals of proceeds (not just token amounts), have real economic substance beyond tax avoidance, and are structured by attorneys who specialize specifically in this area - not general tax preparers or financial advisors trying to earn commissions. If you're considering this route, I'd strongly echo the advice about getting multiple independent opinions. The IRS has significantly increased enforcement in this area, and the penalties for getting it wrong can be severe. Sometimes the most expensive advice is the "free" consultation from someone trying to sell you something.

I dealt with a very similar situation with FanDuel last year - they issued me a W2G showing $12,000 in winnings when I had actually only won about $3,200. What made it worse was that some of the "winnings" they reported were actually just my own deposit money being returned to me after cancelled bets. Here's my advice based on what worked for me: 1. **Document everything meticulously** - Screenshot your entire account history, download all transaction records, save bank statements showing actual deposits to your account. The more evidence you have, the stronger your case. 2. **Be very specific in your communications** - Don't just say "this is wrong." Point to exact transactions, dates, and amounts. I created a spreadsheet showing each discrepancy between their W2G and my actual records. 3. **Escalate strategically** - Start with their tax/compliance department, but if that doesn't work, contact your state gaming commission. I filed a complaint with my state regulator and suddenly FanDuel became much more responsive. 4. **File your taxes correctly regardless** - I used the offset method others mentioned here. Report the full W2G amount but then subtract the incorrect portion with detailed explanation. I attached a 10-page documentation packet to my return and never heard a peep from the IRS. The whole process took about 8 weeks, but FanDuel eventually issued a corrected W2G. Don't let them wear you down - these errors happen more often than they admit, and they have processes to fix them. You just need to be persistent and professional. Good luck!

I'm dealing with something very similar right now with Bovada - they sent me a W2G showing $15,000 in winnings when my actual net winnings were only about $4,200. It's incredibly frustrating because their customer service keeps giving me the runaround. From reading all these responses, it sounds like the key is getting to the right department and being extremely organized with documentation. I'm going to try the approach several people mentioned - bypassing regular customer service and asking specifically for their tax compliance or W2G correction department. One question for those who've been through this successfully: did any of you have to provide additional verification beyond your account records? Bovada is asking me to provide bank statements going back 12 months, which seems excessive for what should be a straightforward correction of their reporting error. Also, for anyone considering the taxr.ai service mentioned earlier - I'm curious if it's worth the cost compared to just organizing the documentation yourself. The peace of mind aspect sounds appealing, but I'm trying to weigh whether it's necessary if I'm already being meticulous with my record-keeping. Thanks to everyone sharing their experiences - it's really helpful to know this isn't uncommon and that there are established ways to handle it properly.

Just to clarify something I learned the hard way... the health insurance coverage question (shared responsibility payment) was effectively eliminated after 2018 due to the Tax Cuts and Jobs Act setting the penalty to $0. So technically you don't have to worry about reporting health insurance coverage on federal taxes anymore, unless you live in a state that has its own individual mandate (like MA, NJ, RI, CA or DC).

Great question! As others have confirmed, since you're a dependent covered under your mom's marketplace plan, you don't need to include the 1095-A on your tax return. Your mom, as the policyholder, is responsible for reporting it on her taxes. Just a couple of things to keep in mind as you file: 1. Make sure you check the box indicating that someone else can claim you as a dependent 2. You'll still report that you had health insurance coverage for the months you were covered (even though there's no federal penalty anymore, it's good practice) 3. Keep a copy of that 1095-A for your records - you never know when you might need it later Since this is only your second time filing, don't stress too much! You're asking the right questions. The main thing is accurately reporting your income from your campus job and correctly indicating your dependent status. The 1095-A situation is entirely your mom's responsibility to handle.

I completely feel your pain with TurboTax this year! I had a similar disaster with their investment import feature - it somehow doubled my dividend income and completely missed several stock splits from my portfolio. What really got me was that I discovered these errors AFTER filing, so now I'm stuck dealing with an amended return. The most frustrating part is that I specifically upgraded to their Premier version because they advertised "seamless investment reporting" - what a joke! I ended up downloading all my tax documents and cross-referencing everything manually, which took an entire weekend. For next year, I'm seriously considering just going with a local CPA who specializes in investment taxes. At least then if something goes wrong, I have someone accountable to work with instead of waiting hours on hold just to be told to buy a more expensive support package.

This thread is incredibly eye-opening! I'm a new community member but had to share my experience because it sounds like TurboTax issues are way more widespread than I thought. I've been putting off doing my taxes because I kept hearing horror stories from friends, but reading all these detailed accounts makes me realize I need to just skip TurboTax entirely this year. I have a fairly complex situation with rental property income, some stock trades, and freelance work - sounds like exactly the type of scenario where their system breaks down. Can anyone recommend which alternative software handles rental property depreciation calculations well? I'm leaning toward just finding a local CPA at this point, but if there's reliable software that actually works correctly, I'd love to save the money. Thanks for all the detailed experiences everyone has shared - this is exactly the kind of real-world feedback you can't get from company websites!

I've been dealing with a similar severance situation and wanted to share what I learned from my tax preparer. One thing that wasn't mentioned yet - if you're making that large December estimated payment, make sure you submit it by January 15th rather than December 31st to get credit for the fourth quarter. Also, when you're calculating whether your withholding from the February severance will cover your first three quarters, remember that the required payment for each quarter is based on 25% of your TOTAL annual tax liability (including the tax on that severance), not just 25% of your regular income tax. Since severance often pushes you into a higher tax bracket, this calculation can be tricky. Your strategy sounds solid overall though. The combination of checking Box D to allocate that February withholding to when it actually occurred, plus making a substantial fourth quarter payment, should definitely help you avoid penalties. Just double-check your math on those quarterly requirements to make sure that February withholding amount is actually large enough to cover the first three quarters!

I've been following this thread closely since I'm dealing with a similar situation - received a large severance payment in March with substantial withholding. One thing I want to add that might help others: when you're using Form 2210 Part III to allocate your withholding to specific quarters, make sure you're also accounting for any regular payroll withholding you had before your layoff. That regular withholding should be spread evenly across the quarters you were employed, while the severance withholding goes in the quarter it actually occurred. Also, for anyone using tax software that's being stubborn about letting you check Box D - sometimes you need to first indicate that you want to complete Form 2210 manually rather than letting the software auto-calculate everything. Look for options like "Override software calculations" or "Manual Form 2210 entry" in your tax program's advanced settings. The severance/withholding timing issue is more common than people realize, especially with all the layoffs that happened recently. It's definitely worth taking the time to get Form 2210 right rather than just accepting whatever penalty the software initially calculates!