Earlier quoted context omitted.
I'm trying to think of places that would want to accept $500 to $1000 notes when many places won't even accept a $50 or $100 and consider them "large bills." While I agree with your premise that inflation makes $500-1,000 notes practical from the standpoint of modern expenses, businesses I interact with tend to prefer a third party to verify payment (CC merchant, cashiers check, etc.). Cash is dying and although I lo…
Cash will continue to be #1 for Craigslist/yard sale-type transactions for a long time I'd say.
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.