Triangle grid using overlapping tiles

I’d like to possibly use Tiled to design/view maps that utilize a triangular grid, where the tiles overlap significantly using alpha transparency. Tiles would overlap over 50% in the X direction and maybe 30% in the Y direction, with an offset to account for the overlap. Half the tiles would be oriented as ‘up’ triangles; other half as ‘down’. It would be nice if the application constrained the two sets to appropriate grid locations, but for basic usage, it would be enough I think to just have the ability to overlap tiles by some specified amount.

My goal is to have a more organic looking map, where the grid is much less obvious, with a top down view. Since render order would impact visual cues, it would be necessary to specify render order per tile layer, where layers are used to organize tile groups by height, with highest tiles rendered last. If the order were predetermined, but just different per layer, that would probably work fine.

A tile would look something like this … 26 x 30 px ‘equilateral’ triangle, 32 x 38 px tile:
+------------------------------+
|X_--^ 6 pixel upper pad.O^--_ |
|+----------------------------+|
| \ . . . <- 30 px ->. . . . / |
|. \ . . . . . . . . . . . ./ /|
| . \ . . . . . . . . . . ./ / |
|. . \ . . . . . . . . . ./ .\ |
|| . .\ . . . . . . . . ./ . / |
|\ . . \ . . . . . . . ./ . | .|
| |. . .\ . . . T . . ./ . .\. |
| | . . .\ . . . . . ./ . O .| |
| \ . O . \ . . . . ./ . . ./ .|
|. \. . . .\ . . . ./ . . .| . |
| . \_ . . .\. . . / . __/ . . |
| X . \_ . . \ . ./ . / . . X .|
| . . . .\_ . \ ./ __/ . . . . |
|- - - - - - - \/ - - - - - - -|
| . . . 6 pixel lower pad . . .|
+------------------------------+

… where X areas are transparent, O areas are overlapping region (mixed transparency), and T area is the ‘required’ opaque triangle part of the tile. “Squished” triangles could be used for a 2.5 D view (though no height would be perceived, only flat). Each tile’s painted region would be roughly a circular … blob.

How difficult would it be to enhance Tiled to support something like this?

  1. overlapping tiles, different X and Y overlap (required)
  2. different render order per tile layer (required)
  3. 2 tile sets, one constrained to ‘up’ grid positions, the other to ‘down’ positions (preferable)

Looks like part of my feature request is covered by this existing issue: https://github.com/bjorn/tiled/issues/871