There I was reading Dan H's blog article on his Parkour Murder Simulator, or rather, on inventing rules to allow a person to play an assassin and something he said really got me thinking. The article says it better but the basic premise is that "D&D doesn't have a skill for Fighting and therefore games based around Stealth shouldn't have a skill for stealth."
Okay, World of Darkness may at first appearance seem to have a Fighting skill but that isn't true. You may roll Brawl but a single success doesn't win you the battle. You have to whittle away their hit points. You get to use Fighting Styles. They get to damage you back. Even in old World of Darkness, combat wasn't as simple as rolling Brawl versus Dodge and he with the higher successes wins.
The trouble with most stealth games is that they're actually poorly supported. There's a single skill with a flimsily applied modifier system for certain specific situations (darkness, concealment, etc.). If you are playing a game that is all about stealth kills, it'd be better to make it a bit more exciting and dramatic than bringing it down to a single roll that either succeeds totally or not at all.
The other thing he mentioned was that, on the other hand, some things should be automatic and therefore shouldn't require a roll. A sailor shouldn't have to roll to climb every single rope they come across while a high school student probably should.
When I'm Storytelling / Dungeon Mastering, I deal with this by allowing players to do certain things automatically when they're tooled in that direction. Oh, so you have several merits based on perception on your nWoD Demon? I'll make others roll for it but you get some of this information for free.
One of the issues I'm having with a character in the next Demon campaign is that he's, well, basically fulfilling the role of an assassin from Assassin's Creed. We have a decent house rule for Stealth Kills that keeps things more involved and less cheesy than a single die roll (one success on three rolls: Dexterity + Stealth, Dexterity + Athletics or Medicine, and Dexterity + Weaponry). But what about when he's running up and down buildings? I don't want him to fall mid-jump every so often because he failed to get a success. True, I could let him do it automatically but doing that too often kind of takes the fun out of having such high skills.
For now I'll probably simply have a failure mean that he has to roll again. If successful than rather than make the jump he drops and grabs the ledge and has to climb back up and try again. At least that way he's not guaranteed to occasionally lose his host due to random happenstance.
I guess I'll have to wait for Dan H's next article on the subject and hope I can steal some grand ideas from it.