Has anyone considered using a 529 plan in this situation? If you're nervous about the market but want to avoid the capital gains hit, could you transfer the UTMA assets to a 529? I've heard this might be possible but not sure about the tax implications.

Something else to consider that might help with your timing decision - if your daughter will graduate in 2-3 years, you could potentially wait until after graduation when she's no longer a full-time student. Once she's not a student, the Kiddie tax rules won't apply even if she's under 24, assuming she's not living with you. This could give you more flexibility on when to realize the gains. However, you'd need to weigh this against your market risk concerns. If you're genuinely worried about a significant market downturn, the tax savings from waiting might not offset potential investment losses. Also, double-check whether your state has any additional considerations for UTMA accounts and capital gains. Some states have their own rules that could affect your decision timing.

Is anyone else noticing that Doordash's in-app mileage tracker is WAY off from actual miles driven? I swear it's undercounting by at least 30% compared to my car's odometer readings.

As someone who's been dealing with gig work taxes for a while, I wanted to add a few practical tips for your situation: Since you're working around health conditions, definitely keep detailed records of any medical appointments that affect your dashing schedule. While you can't deduct the appointments themselves, documenting the impact on your work hours helps explain income fluctuations to the IRS if needed. For mileage tracking, I highly recommend using your phone's GPS and a dedicated app rather than relying on Doordash's built-in tracker - it's notoriously inaccurate. Start tracking from the moment you turn on the app to when you turn it off, even if you're just driving to a better zone. One thing many new dashers miss: you can deduct a portion of your phone bill since you're using it for work. Usually around 30-50% is reasonable depending on how much you dash. Given your health situation and variable income, consider opening a separate savings account just for taxes. Even if you're not making quarterly payments yet, having that money set aside removes the stress of scrambling to pay at tax time. Start with 20-25% of each payout - you can always adjust based on your actual tax liability. The fact that you're thinking about this early puts you ahead of most gig workers. Don't stress too much - the IRS understands that gig income is unpredictable, especially for health reasons.

Has anyone tried just calling Apex Clearing directly? Last year they sent me a corrected 1099 over something stupid, and when I called them, they actually told me the correction was so minor I didn't need to amend. They even emailed me something saying that for my records.

I went through this exact scenario last year with a corrected 1099-MISC from my brokerage. The difference was about $3.50 in dividend income. I called the IRS directly (after waiting forever on hold) and the agent told me that for such small amounts, they don't recommend filing an amendment unless it affects other parts of your return like tax credits or bracket thresholds. The agent explained that their matching system has tolerance levels built in, and tiny discrepancies like this are essentially ignored because the administrative cost exceeds any potential tax recovery. She said to keep both the original and corrected forms in my records just in case, but not to worry about amending. Fast forward to this year - no issues whatsoever. My refund came through normally and I never heard anything about the small discrepancy. So for your 27 cents difference, I'd say don't stress about it. Just keep good records and move on.

Great question about Form 8300! Just to add some clarity - you're correct that you wouldn't need to file Form 8300 in this situation since you're paying by check, not cash. But I wanted to mention something else that might be relevant for your trading card business. If you're regularly buying collections over $10k, you might want to consider whether you need to register as a money services business (MSB) depending on your transaction volume and patterns. It's not common for card dealers, but I've seen cases where high-volume businesses got flagged for not having proper AML (anti-money laundering) procedures in place. Also, make sure you're getting proper documentation for the purchase - receipts, any provenance documentation, photos of high-value items, etc. This protects you if there are ever questions about the legitimacy of the collection or if you need to prove your basis for future sales. The hobbyist angle is interesting too - if they're liquidating a truly personal collection they've held for years, they might qualify for favorable capital gains treatment on their end. Just something to keep in mind if they ask about tax implications of the sale.

Just to piggyback on what everyone's already covered - you're definitely in the clear on Form 8300 since you're paying by check. But as someone who's been in the collectibles space for a while, I'd suggest documenting everything about this transaction really well. Get a detailed inventory list of what you're purchasing, take photos of higher-value items, and keep records of any authentication or grading certificates. This isn't just for tax purposes - it protects you if there are ever insurance claims or disputes about condition/authenticity down the line. Also, since this is a $13.5k purchase from an individual, consider having them sign a simple bill of sale stating they're the rightful owner and have authority to sell. I know it seems obvious, but I've heard horror stories about dealers buying collections that turned out to have ownership issues (divorce proceedings, estate disputes, etc.). A simple document can save you major headaches later. The tax side sounds like it's been well covered by others here, but the business protection angle is just as important for a transaction this size!

I'm dealing with a very similar situation right now with my father's property that I purchased through the Family Opportunity Mortgage program about 2 years ago. One thing I learned from my tax advisor that might help you is to start gathering all your documentation now, especially any improvement receipts and maintenance records. Since you mentioned your mom pays what she can each month, make sure you're properly documenting this as rental income on your taxes if you haven't already. The IRS expects consistency in how you treat the property - if you've been claiming it as a rental (which it technically is since she pays you rent), that actually supports the position that it's an investment property rather than a personal residence. Also, don't forget about depreciation recapture when you sell. If you've been taking depreciation deductions on the property as a rental, you'll need to pay that back at a 25% rate on top of any capital gains. Your timeline of selling next year gives you time to plan for this tax hit - maybe consider spreading the sale across tax years if possible or timing it with other losses to offset the gains. The medical care angle for your mom's move to assisted living is interesting, but as others mentioned, it typically needs to apply to the property owner (you) rather than the resident. Worth exploring with a tax professional though!

I'm in almost the exact same boat with my grandmother's property! Bought it through Family Opportunity Mortgage 2.5 years ago, she's been living there, and now we're looking at assisted living too. One thing I learned from my CPA that might help - make sure you're tracking ANY money you've put into the property beyond the purchase price. I was surprised to learn that even things like the initial utility hookups, property taxes you paid at closing, and title insurance can be added to your cost basis. Every little bit helps reduce that taxable gain. Also, since you mentioned your timeline is next year, you might want to consider the timing within that year. If you have other investments with losses, you could potentially harvest those losses in the same tax year to offset some of the capital gains from the house sale. Just something to think about as you plan the timing. The assisted living transition is tough emotionally and financially. Hang in there - you're doing a great thing for your mom even though the tax situation is complicated.