This is an idea for the LARP, when Weisman inevitably (and, as I'm sure everyone will agree, regrettably) bites the dust.
No one in the LARP has attempted a Caitiff, so why not give it a whurl? What could possibly go wrong?
The main focus point of this character was to play someone who had a clear and defined goal. The LARP tends towards a lot of mucking about, so in the downtimes, it would be nice to have a plot that I can scheme on.
Enter my Caitiff friend, recently arrived from out of town. He's got big plans. BIG plans. His goal is to first establish a domain he can call his own, whether through actual diplomacy or the ever effective "actually I just stay here until you make it official" diplomacy. Crucially though, in the end, it DOES have to be official. he has a strange attraction to being within the establishment's rules, while simultaneously rebelling against them (perhaps his mysterious sire was a Brujah?).
Where will he set up camp? Why, in the only place that takes in the poor, downtrodden souls of the City. The slums. The Rack. The Docklands. Here, he can blend in while gradually learning the ins and outs of the district. Besides, it's very easy to avoid notice or interest when you live in a quarter that no one cares about. And the other Kindred don't care about that place, rather lucky really.
Once set up, he plans to...well, basically start a gang. And gradually bring more and more of the district under his control. One day, provided he lasts that long, he hopes to be the single ruler of the district. he probably won't last that long, but there you are.
How does he plan to go about this? not sure really, but I can tell you how he acts, and that might give some clue. Unlike Weisman, he is none confrontational in other people's turf. In fact, he's quiet, patient, and polite, with an unnerving habit of clinging to shadows to keep out of the way (perhaps his mysterious sire was a Nosferatu?). On his own turf, or when it comes to something that he owns, he acts much more openly and sporadically, flying into fits of rage if insulted or scorned.
but for the most part, he's calm, as he aims to get on everyone's (and failing that, anyone who could give him what he wants) good side. He'll preform odd jobs here and there, sell what he knows at a generous price, and just generally try to make himself as useful as possible until he can stand in his own power base. Hopefully his actions in the Rack will not cause a problem for anyone important, otherwise he might need to wait before doing anything too open...
Oh. Yes. He's ruthless. Absolute stone cold heart. You wouldn't guess it from his first few encounters, but as soon as he feels threatened, like REALLY threatened, he will...overreact. Innocent lives suddenly mean nothing. The Masquerade is now only there to avoid death at the hands of the mortals. So what would be a good ending, if I had the liberty of choosing, would be to have him build his empire in the Slums to NEAR completion, provoking the ire of many another Kindred. leading to an insult in Elysium, and an unfortunate frenzy that ends BADLY. A subsequent shunning of the other Kindred, and then a Blood Hunt when they discover his little secret. pursuit into his territory, cornering him. A battle where he is able to take down a couple of his pursuers. Then Final Death, possibly with Diablerie.
On a cold night, a particular Kindred was engaged in a Blood Hunt. He met one of pursuers, and although he managed to escape, he was badly wounded. Running through the darker parts of town, he happened across an unsuspecting mortal, alone, in a park. Driven by a need to live, he drained the mortal of his blood to heal himself. However, as luck would have it, some of the blood from his injuries made it's way into his prey's mouth. The Hunted was forced to flee further away before he noticed that he had accidentally created a new vampire.