But how about my prisoner suggestion? I realize you got your hands full, but that would be awesome.
I think I'll pass on that one. I've been poking around the prisons and discovering that Bethesda has gotten clever and offered up hidden escape routes which would make a scenario like that not much of a challenge and more of an annoyance. You'd also be screwed in those prisons where the only way to use the hidden escape is to pick a lock and you fail at picking the lock.
Getting out of the city once you've made your way out is pretty challenging though. Even for a veteran character since you'd have to abandon your stuff if you fail to pick the lock on the chest holding your gear.
Any chance you might add an install option that removes the player from the main quest. That is to NOT be the Dragonborn, to NOT have Shouts (or the ability to learn them). This way a player can truly 'live another life'.
For the record, no. The closest I'm looking at going with this is to delay the onset of all that by rigging up the system to leave Helgen intact until you get nabbed in the area and trigger its sequence as normal.
Even that may not happen though. It appears as though vast portions of dialogue and scripting assume you were at Helgen and about to be executed. Makes little sense to go to one of the Jarls and have them commenting about it if those events never happened for you.