1. I modify everything to suit me, and riding vintage provides me with a lot of cheap options. I ride around on a gold women's 3-speed in my jogging clothes, so I have no shame.

On the other hand, I've gotten several complements on my single speed conversion, and I'm finishing up a cool-looking mid-90s Haro. In fact, the 50's clip art lady on the forks informs me that the 4130 Chromoly is both "strong and hard" which is sure to impress fellow riders.

Really, it's less about the bike than it is the ride. Being on the road and having fun speaks way more than the coolness of the bike I'm riding.

2. I have never seen anyone around here ride something like that. Either people ride NEXT bikes or have a recent mid-range Giant, Trek, or Specialized. You can tell the the type of rider from a distance because the former won't be riding properly (middle of foot on pedal, seat too low, never shifts, etc.) and will barely be moving down the road, while the latter maneuvers around traffic effortlessly. I know my LBS mechanic has a Raleigh Sport he converted into a fixie, but I've never seen anyone else riding vintage.