You don't need to invoke hag magic for the warmth. Think Neverwinter in the Forgotten Realms, which is in a not dissimilar northern location - subterranean volcanic heat can help here too. And/Or you could have the seas warmed by the volcanic offshore island on the regional map's edge, with likely more undersea volcanism nearby as well. Warmer seas in a colder climate will give plenty of surface fogs and mists, so all nicely humid, dank and dark (fogs often lift into very low clouds that artificially darken the days, for instance), so also ideal hag territory!

Exactly!

I don't think it really matters what kind of top-down style you choose - even if the settlements are just dots, the pictorial representation shows what's actually there, which is really the point in many respects. The actual region map would really be too small to show pictures of the settlements to scale, so the drawing shows those at the expense of "unrealistic" scenery and scaling instead.

Many of the pictorial styles we routinely use in CC3+ are already a compromise between accurate images and true scaling anyway. Ricko's shown masterfully and repeatedly what can be achieved by ignoring scaling entirely, and going for a purely pictorial representations using those images!

Something you might consider is using this kind of pictorial drawing to illustrate a more traditional top-down map of the same (or a larger) area, in a loose medieval style. Pauline Baynes used this concept to splendid effect on her Middle Earth maps for J R R Tolkien, and her Narnia maps for C S Lewis, for instance, showing images of selected, specific places on the maps.

On the beds subject, I spent part of today constructing a plausible top-down, dungeon-scale view of a four-poster bed, with curtains. Essentially, it's a cutaway, because the top's missing, given seeing where the bed (and anything hidden by the drawn curtains) is more important than that top cover panel (which could be added using a rug/carpet, if available, anyway - or even a repurposed and maybe resized wooden table).

What surprised me a little is there aren't any such beds in the styles I was using (DD3 Dungeons Digital and SS2 Fantasy, so all vector designs); generally, the vector styles have a lot more variety in their symbol options, probably because vector is an easier style to work with/draw in overall, of course. Which at least meant it wasn't that hard to take a suitable bed, and resize different varicolor pieces to work as posts and their feet, with wall-symbol curtains, to create such a bed.

For raster symbols though, it would be great to have some actual options that don't need extra user input!

Having established that I wanted to draw an overground map for Shadow Keep's ruins based on the underground one, I copied and pasted over into a new map the sub-surface wall lines for the Keep's Grand Entrance octagon, and those areas of the Kennels where the hanging moss skeins were shown, together with sketch-lines for where the heaviest collapsed rubble lay, blocking the stairs down into the Grand Entrance chamber, and the first part of the stairs too. That Grand Entrance became the surface ruins' Inner Keep, with a larger octagonal sketch-line for the outside wall of the Outer Keep, together with a couple of similarly sketchy gatehouses for access to both. I also added the line of the Old Road from Elkan Village, leading off the southeast map edge, based on the trail-line illustrated on the Atlas map for the Loksa Environs area (the B&W hex-map from last time).

This looked a complete mess, as sketch-maps often do at first, especially after I started cutting-up the wall-lines, showing which had completely collapsed, and which were still partly intact. I wanted the final walls to look as if they had some surviving dressed stones covering their lower parts in places, with those missing from the higher surviving stones, which I decided would be chiefly packed-rubble wall-cores. These walls were thus initially drawn as stone-fill polygons, so as to have flat sides yet ragged ends where the rest of the wall had fallen away, something simple lines can't do. A couple of higher sheets were added to the stack for numerous hand-placed rock symbols from the Mike Schley SS4 Caves options, sometimes rescaled, with more fallen rock rubble strewn liberally across the ground surface. As so often with elements like this, a degree of trial and error was involved, getting the shadow effects especially to look right, without being too overwhelming or invisible (hopefully!).

The fissures and crevices took still more trials to get right, with various attempts to use bevel options failing to achieve a suitable look, whereas a simple Edge Fade, Inner was all that was really needed, on several dark grey, angular, hand-drawn polygons! In the end, there was so much fallen rubble everywhere, I started to wonder if any of these painstaking efforts would ever be seen at all! At least I'd know they were there though 😁.

Indeed, I scaled-back the amount of rubble, especially over the stairs, since while it's all fine for the map to be accurate, it also needs to be usable for GMs, so things can't always be drawn exactly as they might genuinely appear. In a century since the event, there'd be likely a lot more vegetation covering the rubble than appears here, for instance. Thus, the final map:

As the mapping was underway, I also designed a couple of surface aspects, beyond the heavy vegetation of the Shadow Woods jungle (which was already placed as present on the earlier Atlas map). This was done again using The Tome of Adventure Design, which came up with the Flying Foxes (terrier-sized canines with prehensile forepaws, bat-like wings and sharp teeth, whose bite carries disease - they like to live in the largest jungle trees with big branches they can easily walk along) and the odd-sounding Slap Grass. Slap Grass grows in patches up to adult-human-tall, and crawls along slowly through rubbly soils using its roots. It has sword-length, wing-shaped, flattened flower heads that it uses to slap at passing creatures (attracted by sensing heat and motion from them, if large enough). This forces its seeds into the creature's skin, and if not removed quickly, once in living tissue the seeds grow rapidly through their host's body, killing the creature in a very short time. And, as the yellow-green patches on the map suggests, there's a lot of it about here!

I decided to keep the map overall fairly simple in its labelled features, and not too threatening in its contents, although GMs could always have a few Forager Elemental Wasps pass through as an additional problem for parties trying to clear enough rubble away to access the underground complex.

Looking ahead for next time, it's a return visit to Artemisia, around the south-centre of that island continent, somewhere in the Lampoteuo Region...