Sometimes I wonder the motivation for the "urban pioneers". If that is the lifestyle you want, look to the east coast my friend, its already there. Endless promotion, as in OC, makes me tend to think its about money as much as anything else. Your argument about the newer generation, and permeability, is total BS. Nice thought, I guess. Window dressing, lets be honest.
I grew up in a suburb and found it very boring; thats partly why I now choose to live in East Dallas, Lakewood. While I do like the neighborhood, it is a lot like a suburb, but with some rougher elements interspersed. After all, life's no fun if there's no chance you might get robbed ;)
As far as property values, thats another reason I do choose to live in East Dallas. Your home is one of your biggest investments. I feel that East Dallas will do better than the rest of Dallas long term. Just my opinion. But the endless promotion from some corners is tiresome. There is nothing great about living next to sketchy people.
My grandparents lived in Casa Linda for 80-odd years, and we hated that neighborhood, thought it was hopelessly old fashioned. Funny the cycle at work there.
You'd be surprised how many people living in these places are NOT promoting them. They don't want the places to become Uptown because these places are cool as hell right now as they are. It's not about living an "urban lifestyle." It's about living in cool, creative communities with people who know how those are made and lived. People who really don't GAF about rising property values, if those mean living in ridiculously boring and anti-intellectual places.