Following my test runs with the village of Greenwood Falls (population 920) and Redway Hill Township (population ~3,500), here's my attempt at a major city: Wolfwell Falls (population ~55,000).

This is what Watabou gave me to work with:

And this is what I came up with:

Here's a close-up of the Castle District, which I figure is a bit more upscale.

(I kind of messed up the river there. I when I did the "Change like drawing tool" command, I accidentally wasn't on the River/Water sheet, and I think when I fixed it I messed up the top layer or something.)

The nicer neighborhoods have a lot more greenery. Most neighborhoods have more dirt than greenery, and the area by the docks is muddier.

As predicted in the Redway Hill Towship thread, the longest part was redrawing the secondary roads. According to the Info: Count tool, there are 59 paved roads and 948 unpaved roads! I hope I successfully converted and/or deleted-and-redrew all of the roads. I had to do all of that, and also create a handful of special buildings, before being able to convert everything left to be the regular buildings. If you see any really weird buildings, it might be something I didn't properly convert to whatever it was supposed to be before turning it into a building.

I should draw a lot more fields -- the ones on the north side of the city won't be enough to sustain a city of 55,000 people! (Also, I just noticed that I call it "Wolfwell Hall" on the map instead of Wolfwell Falls. Gotta fix that.)

This was super educational. Thank you! I definitely plan on rewatching. Lots of new commands and techniques to study.

Here are some thoughts I jotted down on potential topics for future Live tutorials. Apologies if some of these exist already (and if they do, could someone point me in the right direction?). If you'd prefer a new thread for these suggestions, please let me know and I can move these suggestions to that thread.

• Build a castle, inside and out (like CA149 Beaumaris Castle) – might require multiple tutorials like the Big City series did.
• Vertical Dungeons / Side Views
• Advanced Drawing Tool Techniques (drawing commands like control-for-smooth with mirrored polygon tools, parabolic polygon, Bezier, cubic poly, chained arc, multipoly tool) – many are mentioned here and there in other tutorials but could be helpful to have a whole video about these techniques to have one video to rewatch.
• Elven Village with connected tree houses (SS5 Elven assets, maybe with a custom-made Rivendell-inspired palace)
• One Day World Builder tutorial video
• CA92 Real World Vector Data (how to import, examples for using like maybe a historical map or a post-apocalyptic map)

I had other ideas, but I think they’re more for future annuals or monthly symbols instead of Live tutorials. I’ll throw them here anyway.

Potential Future Annuals

• Exotic Fantasy Ships (swan boats, gnome dirigibles, eagle-shaped airships, shark-shaped submarines) – feathered/scaly fills, painted wood fills, transparent glass domes (or semi-transparent fills for panes of glass)

Potential Monthly Symbols (possibly an Annual)

• Castle Fixtures, External – Gargoyles & grotesques, flags & flagpoles, spires, bells, drawbridges, machicolations (murder holes), corbels, any other castle ornamentation that could be seen from above
• Heraldry symbols expansion – solid varicolor silhouettes of animals, mythological creatures, zodiac symbols, other common heraldry symbols not currently available in CA15 (great for using as brass inlays or stitched on fabric per this thread)
• Greco-Roman (dungeons & city symbols and fills). Dungeon Symbols: more column options, litters on poles, lounging couches, more statues. City Symbols: various temple types, amphitheaters, aqueducts, Forum…

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.