Does anyone use tax software instead of an accountant? I'm using TurboTax Business for my Schedule C and wonder if the subscription cost is handled the same way. Would I deduct my TurboTax subscription cost on this year's return or next year's?

Great question! I went through this same confusion when I started my consulting business. The key principle everyone's mentioned is correct - you deduct tax prep fees in the year you actually pay them, regardless of which tax year the return covers. One thing I'd add that hasn't been mentioned yet is to keep really good documentation of when you pay these fees. I create a simple spreadsheet each year tracking the date, amount, and what the payment covers (2023 tax prep, estimated payment penalties, etc.). This has been super helpful during tax time and gives me confidence I'm being consistent year over year. Also, if your accountant offers payment plans or lets you pay in installments, each payment gets deducted in the year you make it. So if you paid $400 in December 2023 and $450 in March 2024 for the same tax return, you'd split the deduction across those two tax years accordingly.

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!