With your situation, I'd definitely go with a CPA this year. I was in almost the identical situation last year (job change, stock losses, unemployment) and tried using TurboTax premium. Ended up going to a CPA afterward who found nearly $1,200 in additional deductions TurboTax missed! The COBRA premiums especially - there are special rules about medical expense deductions that the software just doesn't explain well. And with stock losses, a good CPA can help with tax loss harvesting strategies for the future. H&R Block and TurboTax are both fine for simpler returns, but when you have multiple complex elements like yours, the professional guidance is worth every penny.

One thing nobody's mentioned is that you could try a middle-ground approach. Use TurboTax or H&R Block to prepare everything yourself first, then take it to a professional for review. Many CPAs offer a "review service" that costs less than full preparation. This gives you the best of both worlds - you learn how to use the software and understand your tax situation better, but also get professional eyes on it to catch mistakes or missed opportunities. I did this last year and paid $125 for the review instead of $350 for full preparation. If your situation gets simpler next year, you'll have learned enough to possibly handle it yourself with confidence.

For what it's worth, I'm an reseller who gets most inventory from dumpster diving and free piles. I report everything properly on COGS with most items having zero cost basis. Been doing this for 3 years with no issues. The important part is keeping good records of where you acquired items (even if free) and tracking inventory properly. I use a simple spreadsheet with acquisition date, source, cost (often $0), and then selling price when sold.

Wait, I thought Schedule C doesn't even have a place for COGS unless you check the inventory box? If you're getting stuff for free, can't you just leave that box unchecked and avoid the whole COGS section entirely?

Here's what I do as a realtor who drives all over town: I take a picture of my odometer on January 1 and December 31. Then I track only my personal miles (which are way fewer than business) and subtract from the total. I've been doing this for 6 years and had one audit. The IRS agent actually accepted my documentation because I had a calendar showing all my property showings and client meetings, plus gas receipts from the areas I traveled to for work. Just make sure you have some backup documentation that shows you were actually traveling for business.

I've been through 2 IRS audits where they questioned my mileage deduction. Here's what they want to see: 1. Date of each trip 2. Starting and ending locations (addresses) 3. Business purpose of trip 4. Starting and ending odometer OR total miles Don't risk it with shortcuts. My first audit I lost my entire $12,000 mileage deduction because my logs weren't detailed enough. Second time I had proper documentation and passed easily. Just use one of the free apps like MileIQ or TripLog. They run in background on your phone and you just swipe to categorize trips as business or personal. Takes 2 seconds per trip.

One thing nobody's mentioned yet - make sure you're paying quarterly estimated taxes going forward! As a content creator making that kind of money, you should be making payments every quarter to avoid underpayment penalties like you're experiencing now. 2025 estimated tax payment deadlines are April 15, June 15, September 15, and January 15, 2026. Each payment should be roughly 25% of your expected tax liability for the year. TurboTax or any tax software can help calculate what these payments should be. Trust me, it's WAY easier to pay $10k four times a year than scrambling to find $40k all at once!

Since you mentioned having a child, don't forget to look into the Child and Dependent Care Credit if you pay for childcare while you're working on content creation. This is separate from the Child Tax Credit others mentioned. If you pay for daycare, nanny, or other care services so you can work, you can claim up to $3,000 in expenses for one child. Also, as a new parent, start thinking about a 529 college savings plan. Contributions aren't deductible federally, but many states offer tax deductions for contributions, and the growth is tax-free when used for education expenses. It's never too early to start saving!

For what it's worth, I've used both H&R Block in-person and TurboTax over the years. With your situation (married, 4 kids under 16, W-2 income, standard deduction), both should get you the same refund if you enter all your information correctly. The main difference is TurboTax will cost you about $150-200 less. The software asks all the same questions a human preparer would. And yes, your friend might get more from a professional, but that's usually because they have a complex situation (business, investments, etc) where a pro can find obscure deductions.

The biggest thing to watch out for switching from in-person to online is making sure you accurately transfer last year's info. Enter the EXACT SAME personal info (names, SSNs, DOB) as your previous returns to avoid delays.