I'd like to do an Masquerade Game where the PCs start out as Caitiffs are sired by the same person and dumped in a warehouse together with nothing but a note explaining their condition and a vinculum, imposed on them while they were still unconscious, to keep them together. All of the information that could give clues of about the nature of their mutual sire is hidden. They don't know their Generation. I'd keep track of their blood pools.
Of course, they letter that their sire left would explain that all the other vampires probably want them dead, the Cam because they're fledglings without anyone to vouch for them, the Sabbat just because, and everyone for reasons having to do with the identity of their sire.
The punchline, of course, if they do some experimenting to determine their blood pool limits, or if they encounter someone who can read their Generation, is that their Generation is 2.
Which is the sort of thing that makes every vampire organization in the world want to kill them, or worship them, or both. Not to mention that sweet generation reduction that a vampire would get from eating them.
The goal, of course, would be to see how long they'd be able to survive, and how well they'd be able to carve out a niche in vampire society.