LostSoul said:
Hmm... I think you're right when you say it adds more tension. Making more than one check can give you more tension that just rolling one.
It seems that, in my experience, it's
painfully hard to sneak up on a group of people. This would make it nearly impossible.
Also, it seems that being able to sneak up on someone becomes a switch, rather than an opposed roll. If you have to make a number of checks, the Listener has a better chance to hear you (although I'm not sure about the probabilities). So it's not worth attempting
unless your skill is 11 higher than theirs, at which case you can Take 10 and make it all the time.
However... with the penalties for distance, it might work out. Being crap at math, I'd like to see some cases worked out by someone else.
It depends upon the circumstances. For instance, you're scouting ahead in a dungeon corridor. The enemy is not taking care to be particularly silent--in fact, they're talking normally (DC 0) but there's fifty feet between you and them and a corner that the DM decided adds a -2 ad hoc penalty to listen checks. So, if you make a DC 7 listen check (which is pretty darn easy since you maxed listen and you're a wood elf so with you're 12 wisdom, you have a +8 listen check), you'll hear them. Now, you're a second level ranger wearing masterwork studded leather and a masterwork buckler (no armor check penalty), you have an 18 dexterity and 5 ranks each of hide and move silently for a hide/move silently bonus of +9. If you're taking ten, your enemies need a 26 to hear you.
Now, it's a mixed group of orcs up ahead. There are two warriors with alertness and a shaman with a 16 wisdom as well as two barbarians with 4 ranks of listen each. So, their bonuses are +2, +2, +3, +4, and +4. If you're taking ten they have no chance of detecting you.
Of course, you're curious. You can hear voices up ahead but can't understand them (you don't speak orc--just common and elven). So, you creep forward to the corner and peer around it. The corner is only 30 feet away from them and the DM rules that the -2 penalty no longer applies. Fortunately, you get a +10 bonus to hide for just peeking around the corner. So, again, there's no chance that they'll spot you. If you take ten, there's about a 60% chance that none of them will hear you either. (Two need to roll a 20, one a 19, and two an 18--so the chances that none of them will roll what they need are 95%x95%x90%x85%x85%=58.69%). Unless, of course, they're distracted. Maybe they're playing a game of cards and all have -2 on their spot/listen checks. Now, only the two barbarians can possibly hear you and they need to roll a 20 to do so. That gives you about a 90% chance of being able to move up to the corner and see what's there without being spotted.
In either case, you do so and you move back and tell your party about them. Now, you need to decide what to do. You can almost certainly get to within 30 feet of them before being spotted, but if you want to sneak up right next to them and stab them in the back, you'll need to be better than you are.
Change the circumstances. Now, you're a 5th level ranger with a cloak and boots of elvenkind and the same stats, but you have three more ranks. Now your bonus is at +17 each and, as long as the orcs haven't gone up in level, you can sneak up behind them and gank them with your longsword if you want. And they won't be able to spot you... unless there is no concealment for you to hide behind in that last 30' of hallway between the corner and their table.
So, the net result is this: if you take ten, you're guaranteed to be able to sneak up to the difference between their spot/listen and your hide/move silently score x 10 feet of your enemies. If you have +9 and they have +4, you can get to within 50 feet without having to roll. If you have +12 and they have +4, you can get to within 20 feet without having to roll.
You can get another twenty feet pretty easily if the bad guys are distracted, and you have a fair chance of getting ten or twenty feet beyond that. In short, the math doesn't work out to sneaking being a switch. Instead, it works out to be very distance dependent. Sneaking up to forty or fifty feet away is generally easy. However, sneaking up right next to a group of people is hard.
Also, if you're into taking risks--sneaking by people who are good enough that you can't take ten and autosucceed at the distance you're going for, you will sometimes have a better chance of success by rolling than by taking ten. (For instance, if you have +12 hide but your foes have +6 listen and there are six of them, you only have about an 18% chance of making it past all of them by taking ten. But, if you roll and get a 15 or higher, none of them can possibly detect you, so you have a 30% chance of succeeding on your die roll alone and if you don't, there's always a chance they could all roll poorly.