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.

That's just the default option that comes up when you start to save, but it shouldn't be the one you ever choose to use. Just navigate away from that default to save your image files where you need them to be - I use a special set of folders in my Documents folder for ease, for example.

Glad to know you'd got the problem of saving images sorted now at least!

The next step was to add fireplaces to the remaining properties, as their placement determines where the doors, windows and interior walls can go:

The first exterior pathways have been added too, and though it may not be obvious at this resolution, there's a spiral staircase in one corner of the second "under development" house on the left of the street, which will go into the dungeon level below eventually. That mid-building fireplace in the fourth left-side property is going to be interesting to work around!

After adding another descending spiral stair to the fifth left-side structure, I started developing the main bar feature of the series of inn buildings on the street's right side. This also connects with the adjacent property to its northeast, though I haven't finalised exactly what this property will be yet; perhaps another bar-room, or an entertainments room:

The range of fitments in the bar-room are there so I don't later forget what I was meant to be doing here, of course.

And then the inn started to develop in an unexpected direction...

Aside from connecting it to the kitchen-house (first building on the street's right), which was always intended, now there's a fence-enclosed narrow yard, with a latrine block and woodstore, together with a gate nearest the curving road off to the northwest (probably hard to spot at this res).

After which, the pathways around all these right-side buildings were drawn, and some bushes added:

Oh yes, and we now have a stable block for the inn! While it may be hard to tell here, this has been provided with a cobblestone floor, instead of the usual wood planking, and those hay piles look somewhat less strident on higher-res images (I hope!).

Followed swiftly by more external paths, a little more vegetation cover, and a staff house at the east end of the "inn-side" of the street:

Lastly for today's update, are the outer wall and internal fittings for the two northern map-edge properties:

More shortly, with luck!

Yes, those dormers come in very handy for hiding unwanted chimneys; done this myself before for a tropical settlement map in the Atlas!

Often, shadowing problems like this can be improved by softening the appearance of the shadows, to make them more subtle (increased transparency, reduced size, altered colouring, adjusted blurring are all possibilities).

The bridge shadow's showing an odd gap, and its presence illustrates that a shadow effect stacked on another one starts to look odd - the bridge is further from the sea than the cliff bases, yet its shadow is more distinct, for instance.

One option to escape that double-shadowing trap might be to use the existing shadow effect lines and areas to redraw the shadow as a separate polygon, and then turn off the shadow effects entirely. Using one of the "Solid" bitmap fills might work for this, or just a normal darker grey polygon with a suitable transparency effect.

There's also the possibility of adding some extra shadow effects to the little rocks in the sea, as they currently don't have any shadows, which makes them look a little odd where they're exposed to the light. If they're all only low-lying rocks though, they'd cast negligible shadows from this viewpoint anyway, so that may be a shadow effect too far 😉.