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Ive seen many threads about the bounty system and had an interesting idea.
What if when you made a bounty you could set it for dead or alive.
If set for dead then it is a one shot bounty hunter kills person bounty collected debt settled.
Also maybe a time frame so maybe I want him hunted for the next month or 10 kills which ever comes first and have to set up the escrow in advance.
If set alive the player puts in a list of what was lost that he wants back. The bounty collectors job then is to attempt to hunt down the thief and collect what was taken. He may threaten the robber or even just try and find the loot himself to return to the victim. If he kills the aggressor in this bounty. The bounty is closed he may take a faction or reputation hit for not performing it correctly only collects half the bounty the other half is lost and the victim can renew it. This bounty can always be cleared by the thief by returning stolen items to set city and collecting the bounty as a random. So a bandit could exist by stealing and random stuff back to owner.

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Ransom not random.
I see this as being possible, but you could always contact the thief directly and offer to buy it back. Would save you some steps, after all contracts that can suddenly end after being accepted are bad for business.
You hire me to retrieve something from someone through any means necessary, but pay them my fee because they gave it back. I would be cross with you.