Cool! Staring to look better and better, Knightfall!
Oldbridge and Highbridge are the oldest bridges in the city, and thus definitely made of solid dwarven stone. Newbridge is fairly new and made of cast iron, a marvel of modern dwarven engineering. (Newbridge should also be the longest bridge in town, only a little shorter than Oldbridge and Highbridge combined. Any chance of narrowing the river a little at Highbridge?) The other bridges... don't know. Probably stone, I would guess. We don't want to stray *too* far from the medieval city. One cast iron bridge is plenty. Depending on where we place the Glazers, one of the bridges may even be glazed clay bricks, but I don't think we need to go into that kind of detail right now.
I would still move Tradegate further East, but I'll leave that up to you. Dunno how hard it would be to change at this time. (Moves the trade route farther away from the dangerous swamp, and allows us to connect the Squats with the Squats-beyond-the-Wall further downstream.)
Knightfall, how hard would it be to randomly populate these streets with buildings? Is CD2 up to something like that? Or would you need to do lots of work by hand for each individual street? We don't really
need to draw in the buildings (all 5000 of them!

), just curious how powerful this feature is...
The scale in the bottom right is rather hard to read. I'm still wondering exactly how large things are on this map, which is going to become more and more important as we add more detail.
Here's a closeup of how I see Citadel Island. It grew out of the toll gate straddling the trade route in between the two bridges. Then a keep got built next to the toll gate (that's the actual Citadel), and the NE part of the island got split lengthwise into two courtyards where trading caravans can gather before crossing the toll gate. The keep grows as more administrative offices get added, and eventually the entire island gets a curtain wall. I've drawn in a parade ground for official celebrations and jousts etc. There will also be barracks, stables, other administrative buildings etc., none of which I've drawn in yet.