OP I've been a full-time youtuber for 3 years now and the biggest mistake I made was trying to DIY my taxes the first year. Even with all the online advice, I missed so many legit deductions and probably overpaid by thousands $$$. My advice: find a CPA who works with content creators specifically. Regular tax preparers often don't understand our weird mix of expenses and income streams. Might cost $300-500 for tax prep but you'll likely save way more than that in deductions they'll find that you'd miss.

Just my two cents - be careful with deducting things you haven't used yet. My brother got audited last year for his small business and the IRS was particularly interested in equipment he'd purchased but hadn't deployed in his business yet. He ended up having to prove he had a legitimate business need for the items at the time of purchase. He had emails and business plans showing his intent, so he was fine, but it was definitely a stressful experience.

One thing I haven't seen mentioned yet is keeping detailed records of your cleanup and restoration costs too. After Hurricane Michael, I learned that reasonable costs for cleaning, repairs, and even temporary storage while dealing with the damage can sometimes be included in your casualty loss calculation. Also, if you're dealing with contaminated floodwater like you mentioned (sewage backup), make sure to document any health-related expenses from exposure. While medical costs aren't part of the casualty loss itself, they might be deductible as medical expenses if they exceed the threshold. For your antique valuation issue, consider reaching out to local auction houses or estate sale companies. Many of them can provide informal estimates based on photos, and having that professional opinion documented in writing adds credibility to your claim. Even if it's not a formal appraisal, it shows you made a reasonable effort to establish fair market value. The key is showing the IRS that you acted in good faith and used reasonable methods to determine values. Your photos of the damage are actually really valuable evidence that many people forget to take, so you're ahead of the game there.

I want to add something important about the sewage contamination aspect that hasn't been fully addressed. When floodwater contains sewage (which you mentioned), the IRS actually allows you to claim the full replacement cost for certain contaminated items rather than just fair market value, since they're considered a health hazard that can't be properly cleaned. This is particularly relevant for your clothing, mattresses, and upholstered furniture that were soaked in contaminated water. For these items, you can often claim what it would cost to replace them with similar items today, not just their depreciated value before the hurricane. This can significantly increase your deductible loss. You'll want to clearly document which items were exposed to sewage contamination versus clean floodwater. Take photos that show the water line and any visible contamination, and keep records of any professional recommendations you received about disposal of contaminated items. Also, regarding your FEMA payment - make sure you understand exactly what it covered. If FEMA designated some of that $1,350 for specific items (like temporary housing assistance), those amounts might not reduce your casualty loss for different categories of property. You should have received documentation from FEMA breaking down what the payment was intended to cover. Have you considered consulting with a tax professional who specializes in disaster losses? Given the complexity with the sewage contamination and the mix of antiques and regular household items, it might be worth the cost to ensure you're maximizing your legitimate deductions while staying compliant.

As someone who's been through this exact situation, I'd recommend focusing primarily on your mother's passing. A death in the immediate family is one of the few explanations the IRS consistently accepts for penalty abatement. The mail delay from Canada is more subjective and harder to prove without a receipt. Make sure you're using Form 843 for your abatement request and attach a detailed letter explaining both factors. I'd also recommend calling the IRS Taxpayer Advocate Service at 877-777-4778 - they're actually helpful (shocking, I know) and can sometimes expedite these requests when there are extenuating circumstances like a death in the family.

Don't overlook the fact this is your first year filing Form 5500EZ! The IRS has a First-Time Penalty Abatement (FTA) policy that's separate from reasonable cause abatement. You qualify if you: 1) Didn't have to file 5500EZ before 2) Have no penalties in the past 3 years 3) Are compliant with all filing and payment requirements So you actually have THREE strong arguments: bereavement, international mail delay, AND first-time penalty abatement. The FTA is almost automatically granted if you qualify, so definitely lead with that in your request!

Great advice from everyone here! As someone who just started delivery driving myself a few months ago, I want to echo what others have said about setting aside money consistently. One thing that helped me was automating it - I set up my bank account to automatically transfer 22% of every deposit to a separate "tax savings" account. That way I never even see that money as "spendable" and I don't have to remember to manually set it aside each week. Also, don't forget about potential deductions beyond just mileage! I've been able to deduct part of my car insurance, phone bill, and even the insulated delivery bags I bought. Keep receipts for everything remotely work-related. For mileage tracking, I started using a simple voice memo on my phone at the start and end of each shift to record my odometer readings. Takes 5 seconds and gives me a backup if my tracking app ever glitches. The key is finding a system you'll actually stick with consistently! Good luck with your delivery hustle - the flexibility is amazing for college students!

Hey CosmicVoyager! Welcome to the gig economy - it's great that you're thinking about taxes upfront rather than scrambling later like so many of us did! Based on your expected earnings of $200-250/week, you'll likely make around $10,000-13,000 annually. Here's my take after doing delivery work for over a year: **Quarterly Taxes:** With proper mileage tracking, you probably won't hit the $1,000 threshold that requires quarterly payments in your first year. However, I'd still recommend setting aside 20-25% of your gross earnings in a separate account - this covers both self-employment tax (15.3%) and potential income tax. **Essential tracking from day one:** - Mileage (every single mile while the app is on) - All car-related expenses during work hours - Phone bill percentage (you need it for the apps) - Any delivery supplies you purchase **Pro tip:** Download a mileage tracking app before your first delivery and never rely on just one method. I use both an app AND keep a small notebook in my car as backup. Since you mentioned your car isn't great on gas, definitely calculate both the standard mileage deduction AND actual vehicle expenses when tax time comes - you can use whichever method gives you the bigger deduction! The fact that you're asking these questions now puts you way ahead of where most of us started. You've got this!

Don't forget about self-employment taxes! Even if your YouTube business has losses that offset your other 1099 income for income tax purposes, you'll still pay SE tax on the net profit from your existing 1099 work. The SE tax is calculated separately for each Schedule C business - losses from one don't offset SE tax on another. Also, have you looked into an S-Corp election for your profitable 1099 business? At your income level, you might save significantly on SE taxes by taking a reasonable salary plus distributions.

One thing I haven't seen mentioned yet is the importance of timing your equipment purchases strategically. Since you're expecting significant expenses in the early years of your YouTube business, consider using Section 179 expensing or bonus depreciation to deduct the full cost of equipment purchases in the year you buy them, rather than depreciating them over several years. This is especially valuable when you have high income from your other sources that the YouTube losses can offset. For example, if you buy $13.5k worth of camera equipment in year one when your YouTube channel has minimal income, you can potentially deduct the full amount against your W-2 and 1099 income that same year. Also, keep in mind that the IRS looks at the totality of circumstances when determining business vs. hobby status. Even if you show losses in the first few years, factors like time and effort devoted to the activity, expertise you bring, success in similar activities, and expectation of asset appreciation all work in your favor. Since you already have successful business experience with your 1099 work, that demonstrates you understand how to run a profitable business. Just make sure you're treating the YouTube venture like a real business from day one - separate accounts, business plan, marketing efforts, etc. The documentation you create now will be crucial if the IRS ever questions your deductions later.