My nemesis: natural-looking, rolling hills

[Rellek]

Few-months lurker first time poster.

Been working on a slew of maps for my Fantasy TTRPG world. Attached is an unfinished version of a rather large regional map spanning two continents. I'm using Wonderdraft and utilizing most of the AoA assets.

High-res dropbox download

those_damn_hills_1.PNG

The issue that has driven me to seeking guidance is in the title; much of the Eastern side of Kenyérföld is supposed to be rolling hills, broken up with a few spanning forests. However, try as I might, I'm never satisfied with how the hills look. Because of the huge scale of the map, they always end up looking either too sparsely spread out, or too dense. My latest attempt was putting small pockets of hills scattered around the area to try and indicate hills without precisely mapping them. But as you can see without much else in the area it just looks weirdly pocketed.

those_damn_hills_2.PNG

If anyone has any advice or techniques to representing rolling-hills across large areas, it'd be greatly appreciated! I also would love any constructive criticism in general! Please just note that this is an unfinished WIP and additionally some of the perhaps odd-looking choices are intentional. The ridiculously large forest (Draíocht Wilds) to the south is a good example; this area is unexplored by civilization, so in-world cartographers have just estimated it's size and the position of those mountains by sailing around the coast, then filled in the rest with forest.