You get it all-in with the better hand and get offered insurance. (Either by your opponent or by a third party)
How would you determine if the value in insurance is worth the -EV?
I pay for private health insurance as I feel it's worth the value, knowing that it's -EV. Same applies to poker somewhat. But when and for how much? That is my question.
What is insurance? Example:
You have 9h9s, your opponent has 8h8s you go all-in pre-flop for $50 each and you have 82% chance to win. Some other guy tells you: "pay me $20 and i'll pay you the $100 in the pot if you lose". That's insurance.
In this deal, juice (The -EV part of the deal for you) would be about $2. Which is 2% of the pot.