I mean, there's a Harley-Davidson store in the Town Center not too far away from where i'm assuming this will go so I really don't think it's about being fully upscale. Disney Springs would fail if the entire place was upscale. It has to be diverse enough to where there's something for everyone. I'm still waiting for a tech store to come to DS.
Also, no, Ron Jon does not have a location at City Walk. The Surf Shop you're thinking of is Quiet Flight.