Trouble at Durbenford - advice? Also, mounts.

I think the issue with Hide (and any other skill where they might roll multiple times) is that if you have them make multiple rolls, the odds of failure rapidly increase. If someone needs a 5 or better on the d20 to make it (say, DC 20 with Hide +12), he has an 80% chance of succes. If he has to roll twice, that becomes a 64% chance, 3 rolls is 51.2%, 5 rolls is down to less than 33%, etc.

I think to a player, it can then feel like you're rolling until you fail, which is frustrating. Extra frustrating if its out of combat, and you can't take 10, too -- I think that can feel really arbitrary from the other side of the screen.

The game Burning Wheel has some advice/rule called "Let it Ride", wherein the author recommends that you let one roll stand for an entire attempt. I try to apply that as much as I can, because I know I certainly have been guilty of having players roll until they failed in some cases. So, I try and let something ride until circumstances change greatly, or it feels like they succeeded in their initial goal (i.e., if they wanted to sneak to the barn, get there, talk with someone, then decide they need to sneak over the inner palisade and into the bunkhouse, I might ask for a new roll).

The converse of that, though, is that if the player's roll sucked, they are stuck with it. They don't get to roll until they're happy, then let that roll ride; roll and go.

Edit: two more things -- I don't think "Let It Ride" disallows complex or extended checks (a la the UA rules, or some of Spycraft's systems), or 4e-style skill challenges. If you want a situation where it will take X successful skill checks to achieve something, then that's fine. I would say so up front, though; that way the player has a chance to evaluate their odds of success.

Also, another way you could do it is to just make the DC higher; if you want to sneak into a well-guarded castle, and do it with one skill roll, just say the DC is whatever you feel is right, rather than making an interminable series of skill checks (or worse, opposed skill checks).

The bit where the character hides behind a tree, and then walks across an open area, and gets to Hide -- that sounds weird, and wrong, unless I'm misunderstanding. If the open area would otherwise allow a Hide check (e.g., it was dark, and thus offering concealment), I could see where one check might be fine -- but then the whole "hiding behind the tree" thing wasn't needed at all. Open area + dark => you can Hide -- no need for the tree. That's just flavor text, essentially.

But if it's "get behind tree; now I have cover, so I can Hide; now I can carry my Hide roll across this open well-lit area, and no one can see me" -- that's just silly.
 
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