Don't forget that you're only allowed ONE rollover per 12-month period for an HSA! This is a critical point that hasn't been mentioned yet. If you've already done a rollover in the past 12 months, you'll need to use this money for qualified medical expenses to avoid penalties. Also, the 60-day rollover window is strict - no extensions. Calendar those 60 days from when you received the check! Even one day late and you'll face taxes and potentially penalties.

I dealt with a similar situation when I left my job last year! One thing I wish I had known earlier is that you can actually contact Health Equity and request a direct trustee-to-trustee transfer instead of receiving a check. This avoids the 60-day rollover window entirely and doesn't count toward your one-rollover-per-year limit. If you've already received the check, you're still in good shape - just make sure to deposit it into a new HSA within 60 days. I ended up opening an HSA with Fidelity (no fees) and was able to deposit the check there without any issues. The key is making sure your new health plan is HSA-eligible before opening the account. Also, keep detailed records of the rollover process! I saved the original check stub, took photos of the deposit, and kept all correspondence. The IRS doesn't typically ask for this documentation, but it's good to have just in case. Good luck with your decision!

Has anyone used an S-Corp instead of a disregarded LLC to optimize for QBI? I've heard it can be beneficial in some cases.

Great discussion here! As someone who's been dealing with QBI calculations for a few years now, I wanted to add a few practical tips that might help: 1. **Keep detailed records** - The IRS may ask for documentation to support your QBI deduction, especially if you're claiming rental property income qualifies as a business activity. 2. **Consider the timing** - If you're close to the income thresholds, you might be able to defer income or accelerate expenses to stay below the phase-out limits. 3. **Don't forget about state taxes** - As mentioned earlier, most states don't conform to the federal QBI deduction, so make sure you're calculating your state estimated payments on the full income amount. 4. **Form 8995 vs 8995-A** - If your taxable income is below the threshold, you can use the simple Form 8995. Above the threshold, you'll need the more complex Form 8995-A. For your Q4 estimated payment, I'd recommend being conservative and calculating based on your full income, then adjust when you file your return. It's better to get a refund than owe penalties for underpayment. The tools mentioned above (taxr.ai, Claimyr) sound helpful, but also consider consulting with a tax professional who specializes in small business taxes if your situation is complex. The QBI rules are intricate and the cost of getting it wrong can be significant.

I've been following this discussion with interest as someone who works in tax compliance. A few key points to consider: The IRS has been fairly consistent in their position that gambling losses, even for content creators, remain subject to the traditional limitations under Section 165(d). The critical test is whether the primary purpose of the activity is profit from gambling itself versus profit from creating content about gambling. However, there are some legitimate business deductions you might be overlooking: - Equipment costs (cameras, editing software, etc.) - A portion of your home office if used exclusively for content creation - Internet and phone costs related to your business - Professional development (courses on content marketing, etc.) - Banking fees for your business accounts The tricky part is documenting that your betting activity serves a legitimate business purpose beyond just the potential to win money. If you can show that you're placing specific bets solely to demonstrate strategies or create educational content (and you document this thoroughly), you might have a stronger case for some deductions. I'd strongly recommend consulting with a tax professional who has experience with content creators and gambling-related businesses. The penalties for misclassifying gambling losses as business expenses can be significant.

This is a fascinating case that highlights how the tax code hasn't fully caught up with modern content creation business models. While I understand the frustration with the traditional gambling loss limitations, there might be a middle-ground approach worth exploring. Consider documenting a clear separation between "demonstration bets" and any personal gambling. For the bets you place specifically for subscriber content, you could: 1. Use a dedicated business account/card for these transactions 2. Create content BEFORE placing the bet (showing your analysis process) 3. Never cash out winnings from these demonstration bets - instead, use them for additional content 4. Maintain detailed records showing the direct connection between specific bets and specific content pieces While the actual wagered amounts would still likely be treated as gambling activity, this approach could strengthen your position for other related expenses like research time, analysis tools, and the business costs of maintaining separate accounts for content creation. The key is showing the IRS that these aren't just bets you're placing anyway and then creating content about - they're bets placed solely as part of your content creation process with no personal profit motive from the gambling itself. I'd also suggest reaching out to other gambling content creators to see how they've handled this. There might be some informal best practices emerging in your industry that could provide guidance.

Tell your coworker to google "IRS frivolous tax arguments" and look at the official IRS website. They literally have a whole section dedicated to debunking these exact schemes and warning about the $5,000 penalty for submitting these arguments. Also search for "tax protester cases" to see how many people have gone to PRISON for this stuff!

Your instincts are spot on - this is absolutely a scam and your coworker is playing with fire. I work in tax compliance and see the aftermath of these schemes regularly. The "Revocation of Election" is complete nonsense with no legal basis whatsoever. The scary thing is that people can get away with it for a few years, which makes them think they're safe. But the IRS has up to 6 years (or indefinitely in cases of fraud/non-filing) to come after you. When they do, it's devastating - we're talking about accumulated interest, failure-to-file penalties, failure-to-pay penalties, plus that $5,000 frivolous filing penalty for each year. I've seen cases where someone owed $15K in actual taxes but ended up owing over $60K after penalties and interest. Your coworker needs to get back into compliance immediately before this gets worse. The longer he waits, the more expensive this mistake becomes.

As someone who just went through this exact situation last month, I can confirm what everyone is saying - you absolutely need to report ALL dividend income regardless of amount. I had $3.47 in dividends from some leftover stock and initially thought about skipping it, but after doing research (and talking to a tax professional), I learned that the IRS considers any unreported income as potential tax evasion, even tiny amounts. The key thing to remember is that even though your brokerage didn't send you a 1099-DIV, they still reported those payments to the IRS with your SSN. So the IRS knows you received that money, and if you don't report it, their matching systems could flag it later. I ended up calling my brokerage (Schwab) and they were super helpful - didn't need my password, just answered some security questions and they gave me the exact dividend amounts over the phone. Took maybe 10 minutes total. Way easier than trying to reset passwords or worry about whether I was reporting correctly. My advice: just call your brokerage, get the exact amount, and report it. The peace of mind is worth way more than the few cents in additional tax you'll owe!

I'm dealing with a similar situation right now and this thread has been incredibly helpful! I have about $8 in dividends from a Robinhood account that I can't access (phone got stolen and lost my 2FA). After reading everyone's experiences, I'm definitely going to report it rather than risk any issues. The explanation about the $10 threshold being for when companies MUST send forms vs. when WE must report income really cleared up my confusion. I'm going to try calling Robinhood tomorrow to see if they can help me get the exact amount without logging in, like others mentioned worked with their brokerages. If that doesn't work, I'll probably go with one of the AI tax services mentioned here to make sure I'm handling this correctly. Thanks to everyone for sharing their experiences - it's really reassuring to know I'm not the only one dealing with this kind of situation during tax season!