As far as sports town goes, I think the Caps parade and stanley cup craziness that went along with it showed that this is a pretty good sports town. Although I'm not sure a Nats WS would generate as much hype (I think the Caps have been the more popular franchise, even before this year). A skins SB run certainly would though (I'm a Giants fan so I hope this never happens). The wizards are the wizards. Until they pull their heads out of their asses, fire Ernie and change the name of the team they'll never win anything. They changed the name from the Bullets when I was in college and they've been a joke ever since.
Outside of sports DC is a pretty good place to live. I work for the federal gov't and come downtown from alexandria (a real hike, I know) via metro and enjoy coming across the river every day. Not sure I'd want to retire here though. When that ultimately happens for me, I'll be happy to not take metro and/or drive in this traffic for the rest of my life.
I do think something that is underrated about DC is that even though there is a ton of stuff to do right here, you are still close to beaches, a 4-hour train ride to NYC and even shorter ones to Philly, Baltimore, Richmond, etc. Short drive to some cool places in WV and the Shenandoah's.