Sale of goods. I booked a flight for him.
Did you use miles to book it? If yes, and your actual cost was far less than $1000, then unless you had him sign a contract I don't see anything more than a verbal agreement for him to give you $1000. If it were a loan, it would be more enforcible in beis din/court IMO. I'm not saying he doesn't owe you the money, just that it would be hard to enforce.If you booked him a $1000 revenue flight, then of course it would be like a loan.
Offer him a one time deal to pay you back at 50% or whatever you get offered.
Be tofes his teffilin?
You have the wrong strategy. Just post his name and number, and agree to give 30% commission to whoever gets it out of him.
What about embarrassing a fellow yid? He sounds like a guy who got stuck in a bad place, doesn't deserve to have his name dragged through the mud!
Is he giving a reason for not paying back? Like he doesn't have the money or perhaps he feels he doesn't owe it?
Nope. Just keeps saying "you're right I owe you. Will pay you tomorrow, Monday, call me next week" etc. FOR A YEAR.
Being that it's against the terms of most loyalty programs, it may be best not to even try any legal action
I like the idea to grab something Thts his and over to give it back if he pays u let's say a hundred dollars a month for 10 months then give it back. Or even without grabbing try to work out some kinda payment plan.