So i put a Riften jail key in the dresser at the prison you will be in if arrested.. Will the key stay in the dresser or dissapear over time?

I think they respawn but you could just sleep in the bed and be free.

Yes but my rp character is a thief and wishes to escape instead of just leaving and be ''free''

If it respawns then it will respawn after something like 30 days.

You could test it by saving then leave riften and wait 31 days. Then go to Riften jail and see if it is still there. If it is then reload the old save so you don't have lots of hours waited (if you RP anyway).

Ok i will try it. Thanks

No furniture that I have ever seen in the editor respawns. Even in cells that respawn.

Now, I have not looked in the jail, so that could be special cell. But, I would think they would tone down the respawns, because doesn't your equipment get put in a chest or something when you are arrested? I have not been arrested in this game, so not sure.