I'm gonna finish this one now and start another model this evening. I've to speed up, I've only done 18% of arm buildings and I'm going to egypt 1 week tomorrow ^^
one thing to remember, in spring the buildings may be on different types of terrain, and there might be deformation happening. So consider extending the base down a bit when you make buildings.
1 good reason to map cylinders with each face direction layed out flat is if you want to put a gradient shading on the barrel, its hard to do if its just cloned and overlapped.
I'd also suggest to model the cylinder with all necessary cuts first, then unrwap it and deform it after. It's a lot easier to paint then while the little bit of deformation doesn't really hurt.