My idea is that Yaletown itself feels a bit like a university campus. We all live in the same few buildings (dorms ), the seawall is where we all congregate after work, we all go to the same restaurants, know the same people, shop at the same stores. So I think we create a collegiate inspired identity for the neighbourhood.
You could use Yale as a direct aesthetic reference. Create a whole "Yaletown" clothing line of collegiate classics like hats, sweaters, varsity apparel, dog collars etc. I think you make the mascot of Yaletown a puppy named Yuppie (hence we're the Yaletown Yuppies). You could do homecoming parties, and graduation, and formals. I think it would be great.
Secondly, I think yuppie is a wildly under-utilized identity. People still seem to have this outdated idea that it has a negative association. Young, urban, upwardly mobile, professional - where is the insult? I think there is enormous opportunity to reclaim that word into a new status symbol / lifestyle brand