Depends, the insurance industry takes these all the time. Mind you, it's all on their terms, their risks, etc.
Why not, if they're positive EV?
For the insurer: If you're the kind of person who won't blink at paying out $100 you've got better things to do with your time than collecting $10.
For the insured: It's not going to take the sting out of bad news if the payout comes from a loved one anyway. Why would I want to transfer my misfortune to Grandma?
Exactly. I don't want my friendships to have any unnecessary financial constraints. I don't even particularly like to track what people owe at the bar; if I buy you three drinks and you buy me two, you don't owe me anything next time.