Well, you can do the composition on the fly, by having the different sides of the diagonal on different tilemap layers, that'd make things easier, right?
Check my thinking here, but you'll get a checkerboard pattern alternating diagonals, right? Then, I'd suggest
- two layers, 'far' and 'near', for the tile-halves
- a parent 'control' tilemap layer, with ugly editing tiles offset half a tile, (so it gives you a way to draw using the materials you care about) and code to render that into the fragment layers.
It's how this works: https://github.com/aes/autotile3d and it would work.
But then, there's this, I guess: https://youtu.be/dclc8w6JW7Y
Mentioning Blender isn't crazy, one way to make 2d art is to make 3d models and render the poses and orientations you need.