Well the idea originally was that some people would begin of in the prison, but by some I mean only about two. The reason we didn't want to say everyone was already in the jail is that we wanted them to all be new to each other and see how they all interact for the very first time. Dunk picked up on the fact that we could all just be put in a common area where we are forced to interact, but there's a problem with that.
Where is this common place and why have they been put there? Assuming we are sticking as closely as we can to Skyrim's Lore then there is not place that these prisoners could be put, but the man problem is why they've been put there. We really want to emphasise that these prisoners have been left here to die, they don't get let out of their cell to interact with others because nobody cares about them.
We just want to have a bit of variety really guys and we want to see each characters reaction as they are thrown into jail. Maybe if one of you really wants we can have someone already in there who knows the prison inside out or something like that.
Anyway, sorry for the long post.... I tend to ramble on a bit.
Still tell me what you think, it's just having to write about our character getting moved to a meeting place is going to be a pain.