I've been experimenting with three different approaches for adding cliff shadows.

1. Wall Shadow on the sheets with Cliff Symbols: This is the most straightforward approach. However, the shadows render on both sides of the cliff, below it but also above. This can be mitigated by drawing in a terrain mask over the shadow above the cliff on a sheet that is lower in the list than the cliff symbols. In some cases, though, that terrain mask ended up covering up other things. I would have had to do a lot of reordering sheets, which I would have done if this was the nicest-looking approach, but there were other options.
2. Draw in Shadows: This approach is similar to how the shadows on the cliff/riverbanks in Forest Trails are done. There were two ways I could do it: have the shadow layer behind the cliffs, or in front. If they were behind, it covers up any messiness in drawing the shadow, but it also means that the rubble at the base of the cliffs built into the cliff symbols end up "popping" out of the shadow. I could draw it on top of the cliffs but that would require careful work so it's not too messy.
3. Wall Shadow on a Clifftop Terrain. This is the approach used with City Cliffs. That would still require either using a terrain mask, or having the terrain go all the way off the top part of the map, which would require putting those terrain sheets early in the rendering, with the cliffs themselves towards the end. But then I got the idea of trying a SOLID 10 fill instead of grass. Loved it! The Wall Shadow works on the terrain the same way whether it's a grassy fill or the SOLID 10. And the Wall Shadow still worked the same when I made the SOLID 10 only 5% opaque. But I ended up liking it without the transparency, because it made the valley seem more mysterious the higher you go in the mountains.

So here's a screengrab of the types of sheets I set up for each level of the cliffs going higher into the mountains:

There are Clouds sheets but I haven't started to experiment with Alyssa Faden's clouds yet.

Here's a screen grab of what it looks like in CC3, with all of the SOLID 10 layers running off the screen:

And here's how that looks as a JPG export:

The shadows off the cliffs are 35 map units. I could make them longer if you think that's better.

Welcome, Ryan! One more thing, which you might already be planning to do: when you break it down into smaller regional maps, you can then add more details that might be too small for this map. I'm not certain what scale this map is, but for example, this map might only have the major rivers, but smaller rivers and streams might then show up on your regional maps. Or this may only have major cities, with smaller villages and hamlets being too small for this scale until you start to break it down. That gives you the freedom to follow creative inspiration as you dive in deeper.

Looking forward to seeing more!

Because I always have at least three mapping projects going on at once, I decided to work on the interior of my Wizard's Tower while I work through experimenting with three different approaches for cliff shadows for the Hei Shan Si monastery.

I decided to start with the third floor, because that's where the main entrance is. Here, visitors can ring a bell at an outer gate to be admitted into an entry foyer, which has a wardrobe for storing cloaks and such, as well as access to a water closet (complete with a wash basin with water pumped up through an interior well). From there, guests can wait in a waiting room (complete with fireplace) until the wizard is ready to receive them in a more comfortable

Arrow slits allow the wizard or other defenders to guard the tower. The arrow slit that is immediately counterclockwise to the entrance is about waist-high to people on the stairs. The next two counterclockwise would be above anyone on the stairs; the others clockwise would be below the stairs as they continue to ascend. Plenty of magical torches keep the interior bright. In D&D terms, they have been enchanted with a Continual Flame spell that produces a smokeless, heatless flame forever, or until dismissed. (Sure, you have to spend 50 gp in spell components for each, but you'll never have to replace them.) In addition to the exterior stairs, an interior spiral staircase provides interior access to both levels two and four.

This uses Creepy Crypts as the base, with extensive use of Beaumaris Castle assets (plus vegetation from Japanese Temple and furnishings from DD3. And a few tidbits from Forest Trail.

This is the second of three monasteries that I am collaborating with Ricko on. The ideas and text description are Ricko's. The mapping is from me, with his advice, but he is currently traveling and hasn't had a chance to see a lot of the newest stuff. Since he won't be back for nearly a week, I figured I would solicit feedback here in the meantime.

(Also, I have not yet added the clouds that Ricko includes so beautifully in his maps. I will be experimenting with that next.)

There's a full description that will be included when it's submitted for the Atlas, but for now, here's a synopsis:

The Sacred Path of Hei Shan Si

In the heart of the Black Mountains and surrounded by the Ancient Forest, amidst peaks that touch the sky, stands the Hei Shan Si Monastery (Temple of the Black Mountain), a sanctuary of spiritual peace in contrast to the chaos of the surrounding region. Founded by an anonymous sage, the temple is said to have been built with the help of divine forces, its black walls harmonizing with the eternal shadows of the mountains.

The Challenging Path

The road to Hei Shan Si is a test in itself. It begins in the fertile valleys, and ends at the final stop in the village of Yuan Lin Zhen, passing through the living heart of the forest, steep cliffs and narrow trails that wind dangerously through the mountains. Incessant rain, dense fog and biting winds are constant companions of travelers. Worn rope bridges span unfathomable chasms, and legends tell of guardian spirits who punish those who disrespect them.

I didn't have a lot of birds to work with, but I did use the cartouche from Forest Trails and a few other birds from Dundjinni Archives. Like with the last monastery, Chuan Bei Si, the monks use a labyrinth path for meditation (similar to the Labyrinth at the Cathedral of Chartres). But while Chuan Bei Si's stone-and-tile labyrinth is poorly maintained, cracked and worn, the brass-and-tile labyrinth at Hei Shan Si is immaculately maintained.

Clouds are coming, but that will require some experimentation to get it right. They will be on a separate layer that can be toggled on and off.

The funny thing is: although I am not an attorney, my day job in the business side of publishing requires me to be involved in copyright permissioning on a daily basis. Fonts, however, are a new wrinkle for me.