Depicting procedural terrain elevation

Depicting procedural terrain elevation

Okay there aren't a whole lot of places where you can address artists and programmers at the same time so I'm asking here as sort of a last resort before moving on to "Plan B."

I'm in the planning and prototyping stages of making an old-school-inspired RPG. I have both art and programming skills and so I'm doing everything myself once I'm out of prototype phase. It's a little daunting but this is to be a long project anyways.

Anyway here's my problem. Ideally, I want top-down 3/4 perspective hand-drawn all the way for my graphics. Like Zelda or Pokemon, but with vector graphics instead of pixel art. I also want terrain that is procedurally generated, and has some variance to its "height." Ordinarilly, in 2d games, everything is hand-crafted on the map scale. This leads to a large gap between what I can find for tutorials and free art for prototyping, and my final vision for the game. 

All the art I've found is based on a system where all the heights of things are predetermined and really exist in a flattened "walk or no-walk" state. But for my game, I want you to be able to "rotate" the view angle in 90-degree increments, and for the terrain to be actually represented in the data as seperate heights.

At first, I thought I would solve it by using "isometric" perspective inspired terrain tiles. IE, each tile type, instead of having different image for each way it may meet with other tiles, has a top and side to it, and you just simply move up the screen for higher elevations and then draw over the edges on the next row of tiles. However, with 3/4 perspective, nothing looks right. You can never tell where the edges of height areas are.

I think perhaps a combination of the two methods would be best but I just have no frame of reference for it to start from.

Have you ever encountered a similar situation? What should I do? 

Currently, my back up plan is to do the graphics in "isometric" style. It technically would be easier, as I'd have to only draw 2 base facing directions for my character assets, instead of three. (In iso, I can draw facing UP-RIGHT and DOWN-RIGHT and then just flip them, in 3/4 I have to draw UP and DOWN and RIGHT, and then flip RIGHT for LEFT. Assuming both ways I only do 4 directional movement)

If I could just find something similar, though, or maybe just look at it in a different way, Id feel a lot better. I always loved my Pokemon as a child and doing it any other way seems like a copout.