I love Southwest DC. I use to live there when I was in law school and it has many great attributes. The O street area is close to the new baseball stadium and walking distance to shopping, metro rail and the water front. I would just check out your block on Friday night and Saturday night around 11:00 at night to get a true sense of how it is. If you like it and the price is good, then I say go for it.
As a side note, I think this area is poised for terrific growth and appreciation over the next several years. That is, I think where you are considering purchasing will appreciate at a faster rate than the DC market overall.... more