I would think that this idea could be implemented through the Roll20 Rollable Table Tokens method. Wiki docs to help on this idea, Say you create a page with 9 tokens of 31x31 units each, on the Map Layer. If it was as small in acres as the example map (above) this might be as-few-as 2 or 3 map tiles of 31x15 each (based on the appearance of the 'right half' of that wagon-road map). Each token would be a Rollable Table Token with, let's say, perhaps 6 sides each. Each of the 6 sides would be different wilderness map tiles. This is a start, without using API, and already you would have the ability to select all the Rollable Tokens and randomize the 'side' that is showing, thus generating new maps.  From there you could start to build-up the advanced ideas of controlling the terrain variables to influence which Rollable Table Token side is displayed, and, I'm not sure what extent the API can do this part, how complex, or how that would be done.

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To use this, I would probably do 9 tiles of the whole map, that way you could have 'central features' and 'Border features' be more common in different locations. I think you could then have another 9 tile map that is objects. It would be made of transparent tiles that have trees and rocks and such. You could roll all 18 tiles and get random ground associated with random features. The feature layer could also include roads, etc. Could you link the object layer to a lighting layer, so that if the 'Big tree in the middle' tile comes up, a lighting layer that matches it comes up automatically?

That way you could have night wilderness adventures. (I suspect this is script, but doesn't seem too hard.). Photoshop old version free. So, for this to work, there would have to be a 700px x 700px one-px frame that would be identical on each edge, and also be reflectively symmetrical to allow for tile flipping h/v. Then the tiles would end up tiling correctly with whatever aesthetically pleasing fill-in because the blue pixel on the edge of my tile would line up with the blue pixel on the edge of your tile. This would make interchangeable 10x10 square map tiles If you wanted to be able to have pits or lakes, you would need to have the ground tile tell the decoration tile to generate tile 0 (blank) because you don't want trees floating over your pit.

Is the roll20 community a co-productive unit enough that I could put out a frame, and have lots of people do one tile, then everyone just picks and chooses what they like? Or would everyone want to make their micro-sale for the work they've done? Neither is bad, I just would love for this to be a reality.