Indeed, I have had a similar idea in the past myself. However, such an RP is a tad too mundane to be very succesful, no matter how good the players or the host. Fortunately, I do have some suggestions, and an explanation as to why I think that.
I'll start with the explanation then: The escape itself is sound, though it would need an element more than just "Hey, you wanna break out?". That, in itself, isn't a eye-popping, attention grabbing plot, mostly because of how much it has been done. What you need is something exciting to happen, break the tedium, and give us a reason for breaking out, and something to do once that happens.
Now then, my suggestions for how to do this:
First one, the Imperial City is destroyed in some kind of freak accident or natural disaster. This can be anything from Dagon succeeding to an earthquake, it's entirely up to you. I would say that this event somehow causes all the guards to be called away, leaving almost no one keeping watch over us poor prisoners. Or, the incident somehow breaks our cells, freeing us.
But if you don't want something so apocolyptic, why not try something political? If a city is conquered by another country in a war, the prisoners frequently either get freed or re-tried (depending on the attacking party). I say we have the Imperial city be taken by someone like Morrowind, Skyrim, or even just a group of rebel terrorists. Then they free us, if we're willing to help them.
Of course, if that doesn't float your boat, we can always try the good old fashioned divine intervention. A daedric Prince or one of the Nine come to our cells, and tell us they will free us if we do whatever quest they tell us.
I'm scraping the bottom of my on-the-fly idea barrel at this point, so suffice to say that all I mean is that you need a plot beyond the break out. And just trying to find a job while avoiding the police, I'm sorry to say, just doesn't interest me enough. I hate to be so blunt, but I wouldn't join if that's all we had in mind. No offense meant, I'm just saying you need to work on it
I'm sure you can find something suitably amazing, and thanks for posting the idea (you never know if you never try). Keep up the good work :goodjob: