Well, maybe it's personal bias on my end, but I also don't have a positive stereotype of Porsche drivers. But that's beside the point; It's not how the drivers are viewed by others that I'm referring to, but the mindset of the drivers themselves. They both think they have something special, when in reality, their cars are pretty common and difficult to distinguish apart. Go look at the model selection chart for a Challenger and one for a 911 - there are 10 models for different flavors of the challenger, 25 (!!!) for the different flavors of the 911. I'm not talking about different trim levels differentiated by simple optional features, but real powertrain/chassis differences. Granted, the 911 folks has more money to toss around so they get more choices, but the marketing technique these buyers respond to is the same: they think they are special despite having what is a rather common car, and one with a design that hasn't fundamentally changed for a very very long time.
Edit: Let me add, I acknowledge that my stereotype of Porsche drivers is irrational. I'm sure most of them are fine folks.