Quick question related to this - if the OP is getting 1099s from both contract work and ticket sales, does he need to file two separate Schedule Cs or can they be combined since they're both independent contractor type income?

Great thread with lots of helpful info! As someone who's been navigating 1099 contractor taxes for a few years now, I'll add a couple practical tips that might help: For your business exploration expenses - definitely keep detailed records showing your profit motive. I learned this the hard way when I got questioned about some photography equipment purchases. What helped me was creating a simple business journal documenting my activities: dates I worked on the business, what I did, expenses incurred, and income generated. Even failed attempts count if you can show genuine business intent. One thing I wish someone had told me earlier: if you're testing multiple business ideas, consider whether some of them might actually qualify as research and development expenses rather than just business expenses. The tax treatment can sometimes be more favorable. For the ticket reselling - definitely agree with the separate Schedule C advice. I made the mistake of lumping different income streams together my first year and it was a nightmare to untangle. Keep meticulous records of every ticket purchase with the intent to resell, even if you end up using some personally. Also, don't forget about the quarterly estimated tax payments if you're making decent money from both activities. Getting behind on those can be painful come April!

Another option: call the investment company and ask for a draft or preliminary K-1. Many partnerships have rough numbers before the final K-1s are issued. They might not offer this unless you specifically ask, but I've gotten drafts before when I pushed them. Just explain your filing deadline dilemma.

Important detail - make sure to attach a statement to your return explaining the missing K-1 situation if you decide to file with estimates! This has saved me before. Write something like "The K-1 from XYZ Partnership (EIN XX-XXXXXXX) was not provided by the extended filing deadline despite multiple requests. Income reported is estimated based on prior year amounts and will be amended when the K-1 is received." This documentation helps establish good faith compliance.

Make sure to keep copies of EVERYTHING. Print your original return, the new 1040-X, and especially receipts showing the vehicle sales tax you paid. I did a similar amendment last year and the IRS sent me a letter asking for proof of the sales tax.

Hey Zoe! I went through this exact same situation a few months ago. The good news is that filing an amendment isn't as scary as it seems, and it definitely won't trigger an audit just because you're adding a legitimate deduction you forgot. A few things to keep in mind beyond what others have mentioned: 1. Make sure you have your vehicle purchase documentation handy - the sales contract, registration, and any receipts showing the exact sales tax amount. The IRS may ask for proof. 2. Double-check whether claiming the sales tax deduction is actually better than your state income tax deduction. You can only pick one, so run the numbers both ways. 3. When you fill out the 1040-X, be very clear in the explanation section about what you're changing and why. Something like "Adding previously omitted vehicle sales tax of $2,700 to Schedule A itemized deductions." The whole process took about 12 weeks for me to get my additional refund, so don't panic if it takes a while. Just make sure to keep copies of everything you submit!

Has anyone here actually been audited by the IRS for crypto stuff? I'm in a similar situation and I'm worried that if I report a different number than what's on the 1099, it'll trigger an audit.

I went through something very similar when I transferred my Ethereum from Coinbase to Robinhood last year. The key thing to understand is that the IRS matching system will flag discrepancies between what's reported on 1099s and what you file, but that doesn't automatically mean trouble if you can justify the difference. What I did was create a detailed spreadsheet showing the chain of custody for my crypto - original purchase date, amount paid, transaction hashes for the transfer, and screenshots of both platforms showing the same crypto moving between them. When I filed my return, I used Form 8949 with code B and included a brief statement like "Basis corrected - original purchase documentation available upon request." The most important thing is being able to prove this was truly a transfer and not a sale/repurchase. Keep records showing the same wallet addresses, transaction IDs, and timing. If the amounts and dates line up clearly as a transfer, you're in good shape. I never got audited, but I was prepared with a paper trail that clearly showed no taxable event occurred.

Also want to add that if your parents are helping with a home purchase, they could potentially pay money directly to the mortgage company or seller without it counting against the gift limits at all! Payments made directly to educational institutions or medical providers are exempt from gift tax limits.

One more thing - I'm fairly certain the gift exclusion for 2025 is actually $18,000 per person, not $17,000 like someone mentioned earlier. It was $17,000 in 2023, but it increased to $18,000 for 2024 and 2025 due to inflation adjustments. Just wanted to make sure everyone has the correct numbers!