Workflow for side scroller with slopes+variants?

I’ve found Tiled immensely useful for top-down maps, but now I’m working on a side-scrolling game with two different kinds of slopes, and I’m having a difficult time creating maps with my tileset in Tiled. All the automation seems built for top-down maps. I was hoping others might chime in with their workflows for games like this.

Here are the basic tile shapes I’m using, just simple 0:1, 1:2 and 1:4 slope tiles.
(In reality, they’re more complex, as most of these tiles have a matching “top” tile and some have a required “bottom” tile in addition to multiple variant tiles for almost everything.)

My goal is to build naturalistic terrain with lots of little hills and dips. Here’s a screenshot from a test map using the real tiles:

Placing all these little slope bits by hand is a nightmare, but I see no other way to do it within Tiled. The terrain and Wang tools don’t allow setting “empty” as a valid border and I can’t imagine how to achieve slopes with them anyway. Automap is powerful, but requires a base/landmarks to work with, and creating the base is where I’m stuck.

Similarly, those silhouettes of terrain in the background are something I’d love to be abled to “draw” in Tiled, but can’t find any way to ): I am currently building those out by hand, tile-by-tile.

Currently, I’m using an external tool to generate these kinds of terrain and importing the results into Tiled, but it would be really nice to do this work within Tiled so that I can iterate more easily. I feel like I’m just missing some feature(s) or am not thinking creatively enough about the tools I’ve found, since Tiled is so good at everything else.

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Bumping this up because it’s been two years and Tiled has gotten new features. How are y’all handling slope-heavy terrain?

I’ve had some light success with Automapping filling out blocky background terrain, but it doesn’t really help with slopes I need fine control over like the playable ones. I ended up doing all of those with external tools for this game, but I’d really like to not have to do that for future projects.