It looks good! First I tried it with 10-foot wide, 10 degree pitch increments, with a 80 degree pitch at the edges, working up to a 10 degree pitch at the center. The transitions were a little sharp:

Then I redid it with a more gradual transition, 5-feet wide sheets with 5 degree pitch increments going from 85 degree pitch at the edges to 5 degrees at the center. That worked much better! Some fill styles worked better than others, of course -- though some that I didn't care for might be improved if I play with adjusting the scaling. Roof tiles didn't really work very well, but wood worked, as did different stone fills. Here are the top 50% of my experiments:

Thank you for the tip, Sue! I can play with fills (and the scaling of those fills), but I feel like I have something solid to work with here.

So beautiful. You make me want to live in the worlds you paint.

Great! I played with the ADJUST HUE/SATURATION effect to soften the wooden part of the bridge so it blends better. Even though it's unlabeled, I may declare this map is "done" unless anyone else notices anything that needs fixing. Love this style! Thank you to @C.C. Charron, Ralf, and everyone else who had a hand in its creation.

Busy day, so I'm just now getting a chance to get back to this. Don, did you mean something like this, where the foundational towers would extend from the riverbank to rise above the bridge, like the towers of the Golden Gate Bridge, for example?

Okay, I experimented by moving a few of the houses built with the Random Streets tool to a new "BUILDINGS - RANDOM STREETS" sheet. I was able to give these houses greater transparency than the buildings symbols to make them more similar. I also added a COLORIZE effect to make them a little grayer. But this threw off the look of the huts I tested with in the lower left corner that were also built with the Random Streets tool, so I moved those ones to a "BUILDINGS - RANDOM STREETS 2" sheet with a tan colorize effect.

The map is small enough that it's not too difficult to simply replace the random buildings with symbols, but it's an educational exercise to see if I can address it with special effects.

Here's how it turned out, starting with the full map and zooming in. Most of the test houses are in the block directly southwest of the circle part of the canal, with a few others elsewhere to see what they'd look like when the houses were on different terrain.

(Not sure why one of the huts turned browner than the others.)