How about just letting people live where they want to live? I realize this is an academic exercise and shouldn't be taken too seriously, but I think it is an off-putting mentality ("how do we, who are superior because we visit a greenmarket and bike to work, break the bad habits of the proles?") that has been taken up with militant vigor by groups ranging from the StreetsBlog types to DOT officials intent on plopping down TODs wherever possible.
People who read/participate in this and similar fora like cities. It's part of who we are. Other people don't; that's part of who they are. I find it creepy that anyone would consider those who don't want to live in the city dysfunctional or in need of "correction" or "re-education" (after all, the majority of people with children prioritize, for good reason, schools, safe streets, backyards, and the convenience of doing most of your errands in a car that can carry groceries, baseball equipment, backpacks, coffee mugs, and your kids; if most parents prioritized proximity to hipster cafes, we'd end up with a lot more screwed-up future adults).
Moreover, as obvious as this point is, it should be asked: Is there any greater usurpation of an individual's freedom than telling him (or her) where he (or she) must live?
I think Lurker is right in his prescriptions for how to convince people who naturally find cities appealing to move into the city. For the rest of the non-city dwellers (i.e., those who just don't want to live in the city), let them live, just as you would like to be left to live. After all, we don't like it when the likes of Marty Walz try to force those who like city life to live in the suburbs, as it were.
A far more relevant question is: How does Boston become a better city? That itself, without worrying about how to urbanize Newton or Burlington, is difficult enough: residential can't be built near the BCC; nothing can be built near the "Greenway"; nothing is getting built in many infill locations/lots (from the obvious like Filene's to the more complicated like the air rights over the scars created by the Mass Pike or the SE Expressway); and plenty of neighborhoods within the city (the Allston railyards, or across the river in the Northpoint area) are essentially empty.
