Would you accept a $1000 or even $500 note from a craigslist transaction?

I'm usually pretty hesitant to accept anything over a $20 or even deal in cash for small exchanges. I wouldn't even consider $500 unless I had a way to strongly guarentee the bill I'm looking at isn't fake.

It would take a bit of time and research before I felt confident enough at identifying these bills to accept them in a trade. I'd have to do a lot of those sort of peer transactions to warrant the overhead of that time.

unless it's just a one-off purchase, I feel like a much better strategy would be to pay in $20's and have a fraction of them be fake. if someone paid me with a (hypothetical) $500 bill, I damn sure take at least a minute to hold it up to the light and look for security features. they paid me with 25 $20 notes, I would probably just count them and call it a day. if 10-20% of them were fake, I might not realize until I tried to deposit them.

I think it depends on the cost of counterfeiting a single note. All the security features must add up, and I won't be surprised if the cost, unless you're printing literally industrial quantities, makes fake $20 bills unprofitable to make.

Most of the times I've had to use $100 bills at real stores even they didn't check the security features or use a pen. Something like $500 would warrant more checking.

Meet at a bank, works for me

Probably 5 minutes on YouTube and a special pen from Amazon

> It would take a bit of time and research before I felt confident enough at identifying these bills to accept them in a trade.

If such bills were in common use, nearly everybody would know and be aware of the usual security features. So, this is only a problem because such large bills are so rare.

Except that such bills don't see a naturally high amount of use - it's still legal to use them for a bunch of purposes, they're just inconvenient for nearly all uses... Your statement applies better to not-currently circulating modest denominations, like two dollar bills.

Eh last few times I’ve done this I used venmo, works great with strangers too

Why won't use something like Visa Money Transfer?

Because unless you want to read someones multi-page terms and conditions you can never know whether they can claw the money back.