We bought the cheapest house in our neighborhood and we're in the process of "over improving" it ourselves. I don't kid myself about getting all that improvement money back when we sell, because I know what we're doing isn't in line with the neighborhood or the town. I'm doing it because we're going to live here for at least 7-12 more years (we've been here 6 already), maybe longer, and I want to enjoy the improved efficiency and liveability for those years.
I think you're better off with less house in a better neighborhood/community than more house in a lesser area because you can improve your home, but there's only so much you can do about the community around you. And when it comes right down to it, most of the things that matter in a home (schools, playgrounds, recreational opportunities, etc) have more to do with the community than the house itself.