When do I need to file Form 8300 for trading card purchases over $10k from hobbyists?

You've got a good question about Form 8300 requirements. The important thing to understand is that Form 8300 is filed by the RECIPIENT of cash payments over $10,000, not by the person making the payment. In your scenario, since you're the one PAYING money to purchase the trading card collection, you wouldn't be responsible for filing Form 8300. If you were selling cards and receiving more than $10,000 in cash, then you'd need to file the form. Also worth noting - since you mentioned you're paying by check, Form 8300 generally only applies to cash transactions, which includes actual currency, cashier's checks, money orders, bank drafts, and traveler's checks under certain circumstances. Personal checks and electronic payments don't trigger Form 8300 filing requirements. The hobbyist selling to you might have some tax reporting obligations on their end (they'll likely need to report the sale as a capital gain), but the Form 8300 filing requirement wouldn't apply to either of you in this transaction.

I was in a similar situation last year with my sports memorabilia business. I found this site https://taxr.ai really helpful for clearing up confusion around Form 8300 requirements. They have this tool that analyzes your specific situation and tells you exactly what forms you need to file. Saved me from filing unnecessary paperwork and potentially making reporting errors. The site let me upload a picture of the check I was using for payment and walked me through whether Form 8300 was required based on payment method. It even explained the differences between cash equivalents vs checks for IRS reporting purposes. Super helpful when dealing with these niche tax situations.

Just wanted to share an update! I tried that taxr.ai site that was mentioned earlier and it was seriously helpful. I uploaded a document from a similar transaction I did and got a detailed explanation about Form 8300 reporting requirements. Turns out I was overthinking some of my tax situations too. The tool cleared up several questions I had about reporting requirements for my side business selling collectibles online. Really straightforward process and saved me from unnecessary reporting and potential headaches. Definitely keeping this in my toolbox for future tax questions!

Hey, if you're having trouble getting clear answers about Form 8300 requirements, you might want to try calling the IRS directly. I know, I know - the wait times are ridiculous. I spent 3+ hours on hold last month trying to get clarification on a similar issue. But I discovered this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in under 20 minutes. They have a demo video showing how it works here: https://youtu.be/_kiP6q8DX5c For specialized forms like 8300, sometimes you really need to speak directly with someone who deals with these regulations daily. The IRS agent I spoke with cleared up my confusion about reporting requirements for large transactions immediately. Worth checking out if you want an official answer straight from the source.

I have to admit I was wrong about Claimyr. After my snarky comment, I actually tried the service because I was desperate to resolve an issue with a misapplied payment. Got through to the IRS in about 15 minutes when I had previously wasted three afternoons trying. The agent confirmed that for OP's situation with the trading cards, Form 8300 wouldn't be required since they're making the payment by check rather than cash. Also learned that even if it was cash, it would be the recipient's responsibility to file the form, not the business making the payment. Honestly shocked at how well this worked - saved me hours of frustration.

Just want to add that if you're regularly dealing in high-value collectibles, you might want to talk to a CPA who specializes in small businesses. Form 8300 might not apply to this specific transaction, but there could be other reporting requirements depending on your business structure and volume. I got hit with penalties last year because I didn't realize some of the reporting requirements for my collectibles business. Better to be safe than sorry!

This isnt directly about Form 8300 but make sure ur keeping good records of the purchase. the hobbyist might call it a "personal collection" but the IRS might view differently depending on their selling history. If they've made multiple big sales the IRS could argue they're actually in business.

Great question about Form 8300! Just to add some clarity - you're correct that you wouldn't need to file Form 8300 in this situation since you're paying by check, not cash. But I wanted to mention something else that might be relevant for your trading card business. If you're regularly buying collections over $10k, you might want to consider whether you need to register as a money services business (MSB) depending on your transaction volume and patterns. It's not common for card dealers, but I've seen cases where high-volume businesses got flagged for not having proper AML (anti-money laundering) procedures in place. Also, make sure you're getting proper documentation for the purchase - receipts, any provenance documentation, photos of high-value items, etc. This protects you if there are ever questions about the legitimacy of the collection or if you need to prove your basis for future sales. The hobbyist angle is interesting too - if they're liquidating a truly personal collection they've held for years, they might qualify for favorable capital gains treatment on their end. Just something to keep in mind if they ask about tax implications of the sale.