The crappy houses on both sides of the street to the east of Ridgewood will end up being something else sooner or later. If a developer can buy contiguous lots, they could certainly build some low rise or townhomes like the ones Barker is renting further east near Brooks. There will never be a real urban feel to that area though. It's not like Hillsborough which already has a lot of old bones to work with.
As for Meredith, they could've turned the pedestrian gate into a car gate years ago. Pretty sure they like the quaint, secluded feel they have now and don't want to give up most of the (not huge) buffer they've got.