Yeah I am sure that as soon as you can get something as a sample then it will be easier to figure out how easy or difficult it will be to do them. You can post several images which display a bit of each of the things you might want - but at mo I have no real idea what your looking for, or rather I can think of half a dozen styles that it might be. It sounds like an interesting little project. If its very arty then id probably not be the best choice but if more technical / informational then I might have a punt as I think it sounds like you need a lot of them in a uniform style across all the maps which lends itself to a script driven solution which is more my kind of thing and means you can change some part of the style of all the maps in one go.