I'm the poster with the parking space analogy. I'm stupidly psyched that people actually liked my analogy. Thought I'd get flamed for comparing a major purchase to something relatively stupid.
Problem with living in DC, or other major cities: we do have to pay an awful lot for houses that aren't our dream houses. It can be frustrating, if you're from anywhere else, to compare your own home to someone else's from a cheaper market.
I have it easier than some. I'm from a Midwestern city where most of the housing is from decades that weren't that great for architecture. The older houses I do love are in sh*tty school districts. So I'd have a dilemma there too - buy a house I loved in a sh*tty school district (just like DC!) or a house I wasn't excited about in a good one (just like Arlington!) Granted, it would be cheaper, but my salary would be smaller, so it might not seem cheaper.