Would this apply if the stock options were from my employer where I'm just a regular W-2 employee? I don't have any self-employment income or a Schedule C.

No, unfortunately this wouldn't apply in your situation. Since you're a W-2 employee and these were personal investments (even though they were from your employer), you can't deduct these on Schedule C. This strategy only works for self-employed individuals where the investment is directly tied to their business operations. Your best approach is still to add the platform fee to your cost basis as mentioned in the earlier comments, which will reduce your capital gain amount.

I ran the numbers for my situation and it wasn't worth it. Had about $2,700 in investment interest but my total itemized deductions were still about $4k below the standard deduction. Plus you can only deduct investment interest up to the amount of your net investment income, which was another limitation for me.

Thanks for sharing your experience. I was thinking it might be the same for me - probably not worth the extra paperwork if I'm still better off with the standard deduction. Guess I'll stick with adding fees to cost basis where possible and not worry about trying to deduct the interest separately.

I think the Home & Business would actually be perfect for your situation with the online craft sales. It's specifically designed for people with a small business or self-employment income. The Deluxe version doesn't include all the business expense categories and Schedule C support that you probably need. Let me figure out how to get this to you without violating any terms of service. Might need to check what the other commenter mentioned about transfers not being allowed.

Thanks for the info! That makes sense about the Schedule C support. I didn't realize how many business deductions I might be missing with just the Deluxe version. Please let me know what you find out about transferring it.

I second this! Been using FreeTaxUSA for 3 years now. It handles my freelance work and investment accounts perfectly. Federal filing is free and state is only like $15. No idea why people still pay $100+ for TurboTax.

Did you find any good resources for learning about rental property tax treatment? That's my biggest concern with switching from my CPA.

The IRS Publication 527 (Residential Rental Property) is actually pretty readable and covers the basics well. I also found the BiggerPockets forums invaluable for specific rental tax questions - there are both CPAs and experienced landlords who can help with real-world situations. For me, the key was learning about depreciation (which is usually the trickiest part) and keeping meticulous records of expenses. I created a simple spreadsheet where I track every expense by category, which makes tax time much easier. Most tax software has decent guidance on rental properties, but I found that learning the basic concepts first made the whole process less intimidating.

What kinds of deductions did you miss? I'm curious because I'm in a similar boat and wondering what I might be overlooking.

Wait, are you sure the penalty is gone? I thought Biden brought back the healthcare mandate? I've been worried about this for my 2024 taxes.

The federal penalty for not having health insurance (the individual mandate) was reduced to $0 starting in 2019, and that's still the case for federal taxes. The American Rescue Plan didn't reinstate the penalty. Some states like California, Massachusetts, New Jersey, Rhode Island, and DC have their own individual mandates with penalties, so if you live in one of those states, you might still face a state tax penalty. But on your federal return, there's still no penalty for not having coverage.

The federal penalty is $0 now, but it's not an "audit" if they're asking about it - it's just verification. I think the IRS systems still flag returns with no coverage marked, but they don't actually charge a penalty. They just want to make sure you really don't have coverage vs. forgetting to include your insurance info.

That's exactly the kind of distinction I was wondering about! Did you have to provide any specific documentation to the IRS to prove it was a waiver and not a scholarship? My financial aid letter does say "tuition waiver" and "non-disbursing" but I'm worried that might not be enough.

We kept copies of her financial aid award letter that specifically called it a "tuition waiver" and noted it was "non-disbursing." We also kept documentation showing no tuition was ever billed to her student account - just the other expenses like room and board, books, etc. Our accountant said the specific terminology on the financial aid documents is crucial. The fact that yours says "non-disbursing" is very helpful. That's exactly the kind of language that indicates no support was actually provided - there was simply no charge applied. Definitely bring those documents to your accountant appointment!

This is a really good point! The 1098-T reporting can make a huge difference. My son's school didn't include his tuition waiver in Box 5, and we had no issues excluding it from support calculations. But my nephew's university did include his waiver in Box 5, and they ended up having to pay kiddie tax.