Well, at first I'm creating the city to be used in Google Earth. And it's all done using Sketchup. But at a later date, I'm eventually going to use the assets in a game engine. But that's pretty far ahead in time.
During the work with Sketchup and Google Earth, some buildings will probably be repeated. But just a few since this is city that's evolved from scratch about a thousand years ago. Meaning that the buildings aren't even mathematical correct at all.
So I thought I'd use a smart way of texturing to save memory and thus, increasing performance that way. That's why I'm tiling as many textures as possible. The models will be quite simplified and won't have a high polycount at all. At a later date, I'm going to take pictures of the buildings and use CrazyBump to create the bump-maps etc. I've already done some testing on this and the results is very nice indeed!