We thought the windows would make a good first project; they don't require any special equipment, research or extra people, just time, effort, and the cost of caulk and paint. The current "color scheme" (read: lack thereof) is this: reddish standing-seam metal roof, white siding, white trim (such as there is). The windows themselves are white vinyl-clad, so it all kind of blurs together: the windows really recede into the walls, since they're all white and the window trim doesn't stand proud from the wall at all. The obvious fix would be to paint all of the trim some non-white color, but I really dislike colored trim on a white ground. It just looks... eh, to me. What I'm thinking is something like this: the thin piece of trim around each window gets painted black, so that the window 'pops' out from the wall instead of fading into it. The roof goes from a rusty red to a dark charcoal-gray, and when we make the shutters (a whole different project) , we paint them a great denim-like blue. It's the best thing I can think of for a white background. And it's all neutral enough that if we changed the siding color at some point in the future, it would still work.
We have seven windows upstairs, but two of them are really tiny; and four downstairs. It took Don most of Sunday afternoon to scrape and caulk just one. Is every project going to take six times longer than expected?