Demo Man is one of the best on the list, but I don't think it's a $2500 pin. Actually, come to think of it, several of them aren't $2500 pins, unless they are pristine. But that's just me.
I picked WCS for the shot variety, overall speed and the amount of things to do. I would have picked BSD, but there just isn't as much to do in the game once you figure it out.