Why, yes! You would be able to roll for it in one of my games!
Speaking of... I'm looking to run a oneshot this weekend. A quick 3-4 hour adventure. I've run it before and everythings prepared, just gotta find the players for it! So if you're available to start a session between 5-8PM EST on Saturday or 1-8PM EST on Sunday, then check out my thread below!
Yeah, that sucks. I do the "elaborate" thing as well, but that's mostly because i want the player to have a chance to roleplay and give creative input. If they're having trouble coming up with something i'll just try to fill in the gaps.
That or i'm deciding if what they're asking is even possible, in which case they shouldn't roll until after i make the call. ( In general you shouldn't roll unless prompted by your GM)