I don't think my approach can work on yours, as I'm not using the physics plugin... i could be wrong though, if you're doing collision on your own maybe it could.
Anyway, slopes are two factors (dwdx, dwdy) and you may obtain the real height at any point by measuring the distance to the hotspot and multiplying by the appropiate factor, which will give you a dw that you can add to the height.
About sorting, yes: 45� measured to the scene origin, sorting inverted (seeing as the "camera" doesn't really have a position in 3D space). I also thought bottom of top face would be the way to go but, strangely, bottom of bottom face yielded the best results O_o so I'm using that now.