Should skyrim have cellmates that can helpyou break out or be your friends or something?

Maybe as a RE or a perk you can get after you reach a certain mark in the the thieves guild, but not all the time, though i would prefer it to be a RE, maybe the cell mate could have a more fleshed out background and not be some generic pc that is in every prison?

It would be cool if at some point the guy you meet in a prison shows up to your house later in the game and needs a place to stay after escaping. then you can either turn him in or house a escaped convict.

At the begining of the game the prisoner that insults you or tells you to wake up should be in. Other cellmates should be random encounters.

Yeah I think the jail experience could be improved into something cool instead of just sleeping, IDK some sort of mini game while your in prison, you can choose to stay in and do "Jail-type" activities lol?

Brilliant idea! BRILLIANT!

Its very unclear to me on how the game will actually start out, but i have an idea.

You start inside and you meet and greet with a nord prisoner. His attitude toward you could be anything since he will be executed before you do. You two are taken outside to be executed. The prisoner is the first one up that deed is done right in front of you. Then they get you into position, but a man comes out of nowhere and kills the two border guards. That man is Esbern. As for the follow-up story i have no clue.