Well, the way I see it is this, regarding the fort scenario. If we tried to split up, half of us going into the fort and the other half bolting, we would be depending on an exit existing regardless. If anyone goes into the fort, we might as well send everyone into the dungeon. It would be ludicrous to think that half of us could hold the door while the rest come back up after retrieving their possessions, then trying to break out through the camp. Unless some of us make a run for it now, trying to do the above ground route could never realistically work, as the Altmer have had enough time to prepare for us. So, and this is just my opinion, I think we should all just head through the dungeon, then discuss splitting up after we get out the back way. We wouldn't come out far from the camp, so we'll still have to make a break for it, but at least we're not stepping directly into the tents. Regardless of whether one of us knows about a back way, it's a gambit we'll have to take if we want everyone to come out alive.
In character, we can justify the knowledge by interrogating an Altmer on the scene. I don't like the idea of Faendal knowing about it, because if he had known he would have said something about it by now. That's not the kind of thing you leave out of consideration. So, if everyone's okay with that, that's the plan we'll be operating on, for the time being.
And yes, once we reach the city the RP will end, as the escape portion is over. After that we'll wait a week or so for a bit more planning and sign ups, then jump into the next portion.
I imagine we'll arrive in Skyrim by February or so.