Nice Meshon, I look forward to seeing how this works out. I play on a Virtual table top also (Fantasy Grounds 2) and have wondered how to build a cityscape with unambiguous elevation changes too.

I've recently started messing with heightmaps/bumpmaps which I feel could be a good way to do it if used properly and in a subtle way not the typical mountain terrain building way.

I have a finished map I posted today that uses the technique and links to the tutorial I used. (Link in sig to the Sandy Ravine encounter map in my finished maps)

Anyway, look forward to seeing how you work it all out.

If its applicable I could use a technique for a similar situation with a sunken city lying at a 30 degree angle, I have no clue how to depict that in an unambiguous and attractive way on a VTT