Don't forget about 1031 exchanges! If you're planning to buy another investment property, you might be able to defer ALL of your capital gains and depreciation recapture taxes. I've done this twice now with rental properties. The rules are strict though - you need an intermediary to hold the funds, identify potential replacement properties within 45 days, and complete the purchase within 180 days. But it can be a huge tax saver if you're just planning to roll the money into another investment property anyway.

Make sure you're tracking your "selling expenses" separately from your "closing costs" - they're treated a bit differently for tax purposes. Selling expenses (like real estate commissions, advertising, legal fees directly related to the sale) directly reduce your capital gain. Also, don't forget that if you owned and lived in the property as your primary residence for at least 2 of the 5 years before selling, you might qualify for a partial exclusion of capital gains ($250k for single, $500k for married filing jointly) even though it was a rental at the end! This depends on when you converted it from primary residence to rental.

One important thing nobody's mentioned yet - make sure your margin interest is actually for investment purposes! If you've used margin for personal expenses (even temporarily), that portion of the interest isn't deductible. Also, keep in mind that if your investment generates tax-exempt income (like municipal bonds), you can't deduct the margin interest associated with those investments. The IRS has allocation rules if you have both taxable and tax-exempt investment income.

Make sure you keep really good records! I got audited specifically on my investment interest expense deduction last year because I had a large amount ($47k) compared to my portfolio size. Had to provide statements showing all my margin positions and trading activity. The IRS was particularly interested in the connection between my margin use and investment activities. They wanted to confirm I wasn't deducting interest for leverage used for personal expenses.

Make sure you understand the difference between personal items, hobby sales, and business income. Each has different tax implications: Personal items: If sold for less than you paid, generally no tax impact. If sold for more, could be capital gains. Hobby income: Report full amount on Schedule 1, but post-2018 you can't deduct expenses (which sucks). Business income: Report on Schedule C, can deduct all legitimate expenses, but you'll owe self-employment tax. Your situation sounds like a mix of personal items and hobby sales. Document everything!!

I'm dealing with a very similar situation! I've been selling off my vintage video game collection on eBay after years of collecting, and I'm so confused about how to handle this tax-wise. Like you, most of my sales are actually losses when I compare what I originally paid versus what I'm getting now. One thing that's been helpful is creating a simple three-column spreadsheet: Original Purchase Price | Sale Price | Net Gain/Loss. This makes it crystal clear that even though eBay will report the gross sales on the 1099-K, the actual taxable amount should be much lower. I've been reading through all these comments and it sounds like the key is having good documentation. I wish I had kept better records over the years, but I'm doing my best to reconstruct what I can using old credit card statements and checking price history on sites like PriceCharting for video games. The hobby vs. personal property distinction seems really important here. Since you collected these for personal enjoyment and are selling due to space constraints (not to make a profit), it sounds like you have a strong case for treating many of these as personal property sales rather than hobby income. Definitely keep that detailed spreadsheet - it shows you're being thorough and honest about tracking actual gains and losses.

What about expenses though? I deliver for multiple apps too and spend so much on gas and car maintenance that I barely make any profit. Do I still need to pay taxes if my expenses basically cancel out the income?

This is a really common misconception! The $600 threshold only determines whether a company has to send YOU a 1099 form - it has nothing to do with whether the income is taxable. Every dollar you earn from any source is technically taxable income that needs to be reported to the IRS. So yes, you absolutely need to report that $480 from UberEats along with your $780 from Instacart. The fact that they're from different companies doesn't matter - you'll combine all your gig income on Schedule C as self-employment income. Make sure you're tracking your expenses too! Since you're doing delivery work, your biggest deduction will likely be mileage. Keep a log of your business miles for both apps - you can use the standard mileage rate which is currently 67 cents per mile for 2024. Also track other business expenses like phone bills, delivery bags, etc. One more thing - since you're earning over $400 in self-employment income total, you'll also need to pay self-employment taxes (Social Security and Medicare) on top of regular income tax. Consider making quarterly estimated tax payments to avoid penalties next year!

Hey! I was in a similar situation when I started doing freelance work as a student. For the W9 form as a SHEIN campus ambassador: **Business name field**: Leave this blank since you're working as an individual, not a registered business entity. **Federal tax classification**: Check "Individual/sole proprietor or single-member LLC" - this is the standard classification for students doing independent contractor work. Just remember that you'll be classified as an independent contractor (not an employee), so SHEIN will send you a 1099 form if you earn $600+ during the year. You'll need to report this income on your tax return and may owe self-employment taxes if you earn over $400. One tip: start setting aside about 25-30% of whatever you earn for taxes, since they won't be automatically withheld like with a regular job. And keep receipts for any expenses related to your ambassador work (like supplies for events or equipment for content creation) - these can be deducted as business expenses! Good luck with the program - it sounds like an awesome opportunity!

Great advice from everyone here! I went through this exact same process when I started my campus ambassador role last year. One thing I'd add that really helped me was creating a simple spreadsheet to track everything from day one. I set up columns for: date, type of income (commission, bonus, etc.), amount earned, and any expenses. This made filing my taxes so much easier because I had everything organized instead of scrambling to find records later. Also, don't stress too much about the W9 - it's simpler than it looks! The key points everyone mentioned are spot on: leave business name blank, check "Individual/sole proprietor," and use your SSN. SHEIN's payroll team has probably seen hundreds of these from students, so they'll catch any obvious mistakes if you make them. One last tip: if you end up earning decent money from this (like $2000+), consider opening a separate checking account just for your ambassador income and expenses. Makes tracking everything for taxes much cleaner and helps you see exactly how much to set aside for tax payments.