I think I've gotten the wrong end of the stick when it comes to what and when the DM should be calling for rolls when the party is exploring a dungeon.
Picture your typical D&D dungeon crawl. There's winding passageways, a handful of monsters on the prowl, one or two traps and a couple of secrets. My party, understandably, wants to move stealthily, keep an eye out for traps, and watch for secrets. We're playing in roll20 with dynamic lighting on, so they can only see a few squares in all directions, making travel treacherous.
As it stands I end up having them advance a few squares at a time, calling for a new perception check every time they find a new passageway, asking for stealth checks every now and again and having the rogue roll to look for traps each time they wander down a new hall.
This feels clunky, repetitive, and subject to goblin dice. The more they roll, the more likely it is someone will fail badly enough to be spotted by a monster or fall prey to a trap. However, running the entire dungeon on a single set of rolls seems to be against the whole spirit of dungeon crawling; why bother to explore a dungeon at all when a single roll has determined your fate?
I'm aware of the rationale behind long empty hallways in premade maps. In an ideal world you'd design a dungeon crawl that was only rooms, and parcel out your checks per room. But what about a cave system? There's no "rooms", per se... the whole map IS long, possibly empty "hallways". Sometimes you really are trying to navigate a large area with no obvious beginning or end.
I'm sure I'm missing something here... when, and how often, should players be rolling when dungeon crawling?