Carmen, you're definitely not alone in feeling overwhelmed by delivery driver taxes! I just went through this same learning curve last year. One thing I'd add to all the great advice here is to start tracking your income and expenses RIGHT NOW, even if tax season feels far away. I made the mistake of trying to reconstruct everything from memory and bank statements later - it was a nightmare. Create a simple spreadsheet or use an app to log your daily earnings and any business expenses as they happen. Also, since you mentioned you're doing this mostly on weekends, make sure to track those miles even if it feels like "just" weekend work. Weekend driving often means longer distances to busier areas, so those miles really add up! And don't stress too much about getting everything perfect your first year. The IRS understands that gig work is new for a lot of people. Just keep good records and be honest about your income and legitimate business expenses. You've got this!

Carmen, I totally feel your stress about this! I was in the exact same boat when I started doing delivery work. Here's my simplified breakdown for getting started: **Immediate action items:** 1. Download a mileage tracking app TODAY (Stride, MileIQ, or even Google Maps timeline) 2. Start a simple expense log - even just notes in your phone 3. Open a separate savings account and put 25-30% of each week's earnings in there **What you CAN deduct:** - All business miles (including driving to hotspots, between deliveries, etc.) - Hot bags, phone mount, car charger - Portion of phone bill (maybe 20-30% if used primarily for work) - Car washes if done specifically for delivery work - Hand sanitizer, tissues, other supplies **Forms you'll need:** - 1099-NEC from Uber (if you make over $600 total) - Schedule C for your tax return - Form SE for self-employment tax The biggest mistake I made my first year was not tracking miles from day one. Don't be like me! Even if you only work weekends, those miles to busy areas really add up. And remember - you're learning, and that's okay. The IRS isn't trying to trick you, they just want accurate reporting. You've got this! The fact that you're asking these questions now shows you're already ahead of where I was. 🙂

One important thing nobody's mentioned - be careful with the date you claim it became worthless. The IRS is very specific that you must claim it in the year it actually became worthless, not when you discovered it was worthless. From my experience, the reorganization transaction date (your Oct 17) is typically when the broker is recognizing it as worthless, but you should check if that's actually when the company bankruptcy was finalized or if something else happened on that date.

Based on your situation with HealthPlus (HPIQ), it sounds like you're dealing with a classic worthless security scenario. The "Reorganization - 950" transaction on 10/17/2024 is likely when your broker processed the stock as worthless following the bankruptcy proceedings. Here's what you need to do: 1. **Documentation is key** - Contact Schwab immediately and request a letter confirming that HPIQ became worthless on 10/17/2024. Also ask for account statements showing the stock before and after that date. Save any bankruptcy court documents or news articles about HealthPlus's final liquidation. 2. **Report on Schedule D and Form 8949** - You'll need to manually report this since it won't appear on your 1099-B. Use 10/17/2024 as your sale date (not 12/31/2024 as some suggest - use the actual date it became worthless), $0 as the sale price, and your original cost basis. Enter code "W" in column (f) on Form 8949. 3. **Capital loss treatment** - Your $15,800 loss will first offset any capital gains you have this year. Any remaining loss can be deducted up to $3,000 against ordinary income, with the rest carried forward to future years. The fact that HPIQ doesn't appear in Schwab's worthless securities lookup actually supports that it's been officially deemed worthless. Just make sure you have proper documentation before filing, as the IRS scrutinizes worthless security claims closely.

3 Something nobody's mentioned yet - keep a mileage log if you drive as part of your caregiving duties! I deducted over $2,000 last year just from tracking my mileage driving my client to doctor appointments and running errands for them. The IRS mileage rate for 2025 is 65.5 cents per mile.

One important thing to consider is whether you should be classified as a household employee versus self-employed. Since the family is claiming you on their taxes for a dependent care credit, they might actually be required to treat you as a household employee and handle payroll taxes. If you're a household employee, they should be withholding and paying Social Security and Medicare taxes on your behalf. However, if you control how and when you work (set your own schedule, use your own supplies, etc.), you're likely self-employed. For $15,300 in annual income, you'll definitely want to make quarterly estimated tax payments to avoid penalties. I'd recommend setting aside at least 25-30% of each payment to cover both self-employment tax and income tax. Don't forget you can deduct legitimate business expenses like mileage, supplies, and any training related to caregiving. You should also check if the family needs to provide you with any tax documents - they may need to give you information for their dependent care credit claim even if they don't issue a 1099.

I'm in a similar situation but we solved it by having all beneficiaries make small annual contributions to the trust for "maintenance fees." It's way below market rate rent, but our attorney said it helps establish that we're not just getting completely free use which could be viewed as distributions.

This is a complex area where the facts really matter. Based on what you've described, the trust paying for basic property maintenance expenses (taxes, utilities, insurance) on property it owns would typically be considered trust expenses rather than distributions to beneficiaries. The trust is maintaining its own asset. However, the free use of the property by beneficiaries could potentially create imputed income issues. The IRS could argue that the fair rental value of your usage represents a distribution to you. This is especially true if the usage is significant or if certain expenses are more "personal" in nature (like premium cable packages). Key considerations: Does your trust document explicitly allow beneficiary use without compensation? How many days per year does each beneficiary use the property? Are there any expenses that are clearly for beneficiary convenience rather than property maintenance? I'd strongly recommend having your trustee consult with a tax attorney who specializes in trust taxation. The $28,000 annual expense level makes this worth getting right, and the stakes are high enough that professional guidance would be money well spent.

I want to add another important consideration that hasn't been mentioned yet - the timing of when you recognize your trading gains and losses for tax purposes. Since you mentioned you've been "tracking everything meticulously," make sure you understand that for tax purposes, you generally recognize gains and losses when you close positions, not when you open them. This is crucial for your quarterly estimated tax planning because if you have large unrealized gains in open positions, you won't owe taxes on those until you actually close them. Conversely, if you have unrealized losses, you can't use them to offset your tax liability until you realize them. Given that you're 8 months into the year with $78K in profits, I'd also suggest setting aside a separate "tax account" going forward - maybe 35-40% of each month's realized profits - so you're not scrambling to find cash for tax payments. Many full-time traders get caught off guard by the cash flow impact of quarterly payments, especially if they've reinvested their profits back into trading. One more tip: keep detailed records of all your trading-related expenses (platform fees, data subscriptions, home office costs, etc.) as these can significantly reduce your taxable income, whether you qualify for trader tax status or not.

Jumping in as someone who went through this exact transition from corporate job to full-time trading last year! A few additional points that might help: 1. **Safe Harbor Rule**: Since you mentioned this is new territory, the "safe harbor" rule is your best friend. If you pay 100% of last year's total tax liability spread across four quarterly payments (110% if your prior year AGI was over $150K), you're protected from underpayment penalties regardless of how much you make this year. This gives you peace of mind while you figure out your trading tax situation. 2. **Self-Employment Tax Nuance**: Be careful about that 14.13% self-employment tax calculation mentioned earlier. If you qualify for trader tax status, your trading profits might NOT be subject to self-employment tax - they'd be treated as capital gains instead. This could save you thousands. But if you're just considered an "investor" (even an active one), then yes, you might owe SE tax. 3. **Quarterly Payment Timing**: Don't stress too much about perfect quarterly amounts. I made uneven payments my first year based on actual performance each quarter, and it worked fine. The key is making sure your total payments for the year meet the safe harbor threshold. Since you're already 8 months in with solid profits, I'd calculate 25% of last year's total tax liability and make that payment for Q3 (September 15), then reassess for Q4 based on how the rest of the year goes. This approach has saved me from both penalties and overpaying. Good luck with the transition - it's definitely manageable once you get the system down!