Agamon
Adventurer
This is so not covered by The Rule of Cool.
DM: You arrive at the village. The guard motions for you to enter. There's no gate; they throw down a rope.
Player A: A rope? The hell? Alright, I guess I try to drag my platemailed-butt up there... nope, missed the roll. I fall down on my arse. Guess I'll keep trying. Hope I don't die trying to enter the village.
Player B: Not me! I tie it to my ankle. They can haul me up like a sack of potatoes. Slowly.
Player C: I'm not leaving my horse out here.
Cool heroic fantasy this ain't.
You need to roll to do this? Personally, I don't micromanage so much, this would be handwaved unless it made for an interesting plot point for some reason.