Yeah one of the best aspects of the game is that you will not loose out of content if you fail a speech check. If anything, you loose out of content by hitting the check. I have yet to find a situation that cannot be solved several other ways if I fail a check. That being said, I agree you should not have to roll several times to achieve one thing. It makes me think of a new DM who forces the rogue to roll a stealth check for every guard he sneaks past on his way to X location.
I think you also need to roll new stealth checks for every round in this game. And if combat is going on for some party members, but others are still sneaking, the sneaking ones still continuously roll stealth checks until they fail them, even if combat is paused.
I should test this out, though, that's a good idea.
EDIT: Indeed, when sneaking inside someone's cone of vision, you constantly, without pause, roll Stealth checks until you leave the cone, or you fail. Whether you are in combat or not.
It's not that the enemies each get to make a perception check once a round either. That's normal and expected.
