The bounty system is kind of nonfunctional. It is in essence a butthurt register - if you don't like someone, you place a bounty upon them, and when they get killed by anther player, he makes some money. Ideally this should encourage bounty hunting, but in reality, the majority of bounties are so pathetically low that it doesn't even encourage suicide ganking. The other limit is that only a percentage of the bounty gets paid out, so unless the maths are spectacularly fortuitious (billion ISK bounty on a guy in a shuttle hauling PLEX) you only get a fraction of the pool, especially in company with friends because it is split.
So the whole Retribution expansion should have been named Petulance. There's absolutely no point in putting a bounty on someone other than to register your displeasure.
So, last night a guy in a Mackinaw registered his displeasure with me for destroying his ship. I mean, OK, so maybe he got bumped 25km away from his tractor and maybe I was in the process of destroying it with me Nereus, but he did have a ship scanner, he did not have to sic his drones onto me while in scram range, and he could have done what everyone else does, which is warp off and back to the tractor at zero and scoop it. So he died, got podded, and eventually lost the tractor too.
This earned me a 10M ISK bounty, which you are all free to collect, and merely loses this guy 10M more ISK when you think about it.
The other thing is killrights. I earned a killright against myself for attempting to suicide a guy's Wreathe in highsec. I failed due to forgetting a scram in my rush, which is irrelevant anyway. He put my right out for 30M ISK - so he earns 30M ISK if anyone activates it.
In this case, it is an interesting bit of game theory at play. On the one hand, any self-respecting spacefiend will just buy off a killright (earning the previous victim a bit of ISK) and blow up a shuttle, extinguishing it. An active killright is potentially a problem for you if you transit the market hubs and pipes in something non-cloaky, fat, and expensive. Marmites or the general public may see your killright and pay to kill you.
The interesting dynamic is this. Lets say I'm actually happy to have killrights on my head, because it makes highsec exciting. I mean, here I am tooling about in a hauler, shooting Tractors and looting wrecks and flipping cans just to get aggro I can then use in a structured fashion to enter engagements of my choosing, and farm awesome killmails (and one day, FRAPS the results and make a YouTube channel). I'm not really held back by a killright - in fact, if the right is cheap enough, I may pay multiple times to trigger it, to spawn a suspect timer so I can get a fight.
So it becomes kind of a mini-game and a psychological shadow-boxing game. If you set the right too high, the guy with the right won't buy it out, and neither will Marmites. But then again, some people expressly set their rights open at 1B ISK hoping to get a big payout from someone who mistakenly clicks yes on a 1B ISK right.
Then again...again...it all depends what you fly. Undock in a Vindicator on station with a 250M ISK killright and you're more likely to get it activated. Dock up immediately and undock a shuttle and it's gone - and someone's made 250M ISK. Gamed.
Then again again...again...250M ISK or it seems, even 30M, when you primarily fly frigs and haulers around (esp. a Nereus) sees no one activate it, resulting in the holder of the right not making much money, and the recipient not getting much pew pew.
All in all, I would definitely suggest opening conversations with the right holder if possible and negotiating a value for the killright on your head which suits both parties. It is, in some way, in the interest of the right holder to get the right activated multiple times without the recipient being killed; he gets paid multiple times. The recipient gets multiple engagements in hisec (and, i guess, lowsec), and gets pew pew.
I doubt this will be a common occurrence. Most holders of killrights are also nursing a hulk loss and inflamed buttocks. They're just as likely to Q.Q as to collaborate with a ganker to farm ISK on the killright.