Oh. I'm the first voter.
Yeah.
OK, so I voted "no" for the whole thing. Trying to make a city from a Firstperson-RPG view/gamestyle is just too weird. Seriously, how are you going to place buildings? Manage books? Staff? Plant tress/shrub, etc?
I'm sorry, but it's not the right game for this.
bloodmoon didnt do TOO badly with it... you could choose where your own house would be built by finding different torches placed around at building spots, i think... you could decide from a handful of spots, im pretty sure.
so... it could be done, but bethesda would need to choose a specific area of land for this town to be possible at, or multiple areas... and everything would need to be planned ahead by them, several spots made available for buildings to be placed, etc...
still, that'd take alot of work, and would distract them from the main game, most likely... so it probably wont be in skyrim, maybe in a future TES game.
saying something like this is too weird for TES is like saying having children in the game is too weird for TES... oh, look, children are already in!
so are several other things people wouldnt have ever expected.