However, I have a more negative view for the future of Westchester. The constant airplanes flying overhead have been a huge deal breaker for people that I have shown condos to in that area.
There are plenty of areas surrounding Westchester that are great choices like Playa Del Rey.
That's just my opinion, hope that helps!
As far as future plans for a cohesive "downtown" area, there is always discussion about this at the city meetings. I think it would be a great idea, and increase property values for the neighborhood. If you buy in the area, you can join the discussion about this.
Culver City had a budget for this when the re development agency made the sweeping changes in Culver City only five years ago. It surely can be done, in any area
Less privacy and less communication between neighbors. Allot more technology in home protection. Possibly portions of the community forming gated areas, HOA's taking charge of security and upkeep. Most everyone in Westchester has a gardener.
Shopping: it is getting better for bargain stores, but not many higher end boutique type stores. Even locally, nearby there isn't much.