Thinking further about this option since the livestream, it's a powerful tool no matter what kind of settlement you're wanting to map, even if it's to fit in a pre-drawn setting, as anything unwanted the random option generates can be readily moved or removed to fit terrain features (e.g. coastlines, rivers, cliffs).

Different areas of a larger city could be created randomly in different ways (medieval and modern could be mixed, drawn from different random maps, for instance), and then fitted together in a suitable CC3+ master file, simply by copying over the relevant parts of the separate randomly-created settlements.

Naturally, this would need quite a degree of restructuring and amending after the fact to make everything fit together correctly, although a lot of the base work would be done from the random creations.

It would also be possible to "super-detail" parts of a settlement drawn in a quite different style, such as a Watabou-type settlement, leaving the "blank" areas for segments that weren't necessary for such detailing. Again, unwanted parts of the random design would need removing, but this would be something to consider if of interest.

Just time to generate a quick sample random city map before the stream (it may not take anything like that long, depending how long you take adjusting the parameters first)!

While tinkering along the northern, east-street area, I'd started wondering how viable those narrow strips of grass might be along the southeastern side, and even if I should remove the bushes and thin grass verges on the other. Currently, I've opted to maintain the bushy verges (makes sneaking around the front of the inn easier for nefarious purposes, after all!), but have "paved" the other side's verges with a fresh area of dirt trackway.

To make up for the loss of vegetation cover, some new garden plots have been set up (not all with their vegetation added at this stage), together with a battered, earthen area between the curving road and the back gate of the inn's yard, which seemed a natural addition, using the same dirt fill as the gardens, with much less vegetation cover. The perceptive may notice I've also now added a lot more small, low-growing, "dots" of meant-to-be weeds in numerous places, helping break-up the textures and some of the harder pathway edges in places.

Now the rest of the garden plots northwest of the inn street have been finished, it's perhaps a little easier to see that vague, not-yet-pathway from the road to the back of the inn:

Which leaves just one last row of buildings to design internally, and a few more garden plots to add. This was as far as I got in my most recent session:

The non-spiral staircases have been a little bit of a battle all the way through. The initial trio all had the same orientation, so could be easily copied from one place to the next and still have their effects look correct, although even then, the second one had to have its staircase symbol adjusted for size (which luckily meant it fitted better to the third house as well).

Those in the two houses west of the main road though were in an opposite orientation, and needed to be added to a new sheet with altered effects to stop their shadows protruding through the solid wall they're inside. With those alternatives in-place, the two new staircases on the inn street were less of a problem in that way, for all adjustments to the shade angle have been necessary for nearly all the "landing" floor pieces, to get them to work with their lower floor planking as well.

One other thing was corrected. For some reason, all the doors and windows in the northwesternmost property of the "temple square" section (closest to the south corner of the first house on the south side of the inn street), had ended-up on the wrong sheet, and were casting wall-level shadows. That was spotted because I normally use the "eye-dropper", :CC2KEEP:, to set-up for whatever items I'm next drawing in a map like this, which provides a quick means to do so (especially for Layers, which aren't always automatically associated with symbols, for instance), and a check for mistakes - as here.

Nearly done now, at least for this first mapped level...

If you're wanting to darken the entire map, it may be possible to achieve something approximating your second image by setting up the effects as Sue was showing, but using the "Whole drawing" radio button, instead of just for one selected sheet. This can have unwanted consequences, depending on what your original map was like, but it is probably experimenting with at this early stage.

You're not alone in battering away at unwanted nodes to get rid of them! I usually end up hiding or freezing any overlapping entities (like the LAND sheet here), and then just clicking to remove a node or two nearby more or less at random till something useful happens (and using "Undo" if it makes things worse!). Of course, the trick is then to unhide the LAND sheet and lose the same nodes in that, otherwise, as Sue said, the outline may no longer match the landmass...