Is this from the non-ProFantasy Harn Style of CC3+ mapping developed by Roy Denton? I don't actually have this installed, so can't really help, but if it is, I know a few of our longer-standing Forum contributors do, so can hopefully assist.

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!

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 😉.