I may have found a cool city map building trick in inkscape

[ravells]

Bryce has a similar thing for 3d objects. I thought it would be a good city creator but I think I began to run into the same sorts of problems you're doing....hopefully you'll find an ingenious solution!

[Notsonoble]

Right now, it's "let it scatter them to the winds, or clump them... and then make adjustments..."

If you did buildings that didn't come pre shaded (the ones I'm playing with are), and perhaps did a bunch at a wide range on the rotation tab... you could do a lot better...

Unfortunately... this is my last week at my current job, which is followed by a week of (already planned) vacation away from computers, followed by a new job that's a completely different shift, and in a completely different town(s).

So I probably won't be able to hit this again until July -_-.