Aen made something like this for me a few months ago, which took a gif and made a map with a tile for every different color on the map.
So I went from
[this]
To these:
[1] [2] [3]
With very little hassle.
Also, as far as making advanced map import utilities... I was thinking that making a PSD->Map utility would be the bizzity bomb. It'd create all the unique tiles needed for every layer, add them to a vsp, and create each layer as appropriate from the layers order. Hell, you could even have it do the same for the Obs layer as long as you named one of your layers (or better yet, masks) 'obstructions'.
That'd probably be the greatest benefit in the world to a pure artist trying to make a map.
Is this what you meant?