I know I am coming in late. I've tried to read all the posts carefully so I apologize if my advice below duplicates something that has already been said.
But first, I just want to say: this has been a fascinating but also frustrating thread.
As with many threads, things that are common in many large metro areas are portrayed as unique problems to Pittsburgh. These include: difficulty in walking to suburban shopping centers; the decline of neighborhood grocery stores; the fact that most of the population would rather drive to work or the grocery store than take public transit or walk; the fact that public transit is mainly designed for suburb to downtown commutes, etc. I should like to add that the OP will find it difficult to live in Pittsburgh because of global warming. and because the most recent Woody Allen films shown here have been disappointing.
As I understand it, lostinpgh wants to get by with one car, to live in close proximity to food stores and bookstores (as a proxy measure for quality of life), and wants to have a relatively easy commute to Oakland (for now) and then to Lawrenceville. Her husband will commute to California PA by car. They wouldn't mind living somewhere close to California but they prioritize a walkable neighborhood and access to public transit over saving a few minutes in the car for him.
Do I have this right?
I can think of two areas they should look:
1) Arguments for Squirrel Hill (or Point Breeze or parts of Greenfield):
--a Giant Eagle in the center of Squirrel Hill
--another Giant Eagle in Greenfield for those on the southern edge
--relatively close proximity to Whole Foods, Trader Joes, and the East End Co-op on the Point Breeze side of the neighborhood
--an actual greengrocer on the lower end of Murray Ave
--sidewalks throughout
--a Barnes and Noble in Squirrel Hill; a Borders in East Libery
--two movie theaters in Squirrel Hill
--lots of restaurants
--local and walkable service-type stores and professionals--dry cleaners, shoe repair, tailors, opticians, dentists, pediatricians, internists, CPAs, etc. even a mechanic in Greenfield so you can walk to pick up the car when it's in the shop
--good public schools in the Colfax/Minadeo feeder patterns
--good public transit to Oakland (and let us assume that UPMC will indeed come up with a solution for Lawrenceville; I also would not be surprised if the Port Authority altered some of its East End routes when the new hospital opens to get closer to the entrance)
googlemaps gives a 52 minutes driving time from Squirrel Hill to California. I believe that at one point lostinpgh suggested that her husband would mainly be going offpeak
(By the way, googlemaps gives 46 minutes from Mt Lebanon. To save 15 minutes a day, you all are going to send these folks to the South Hills?)
Yes, I do know that there are many other places in the Pittsburgh area that are nice places to live. And yes, I know that always recommending Squirrel Hill makes some of us seem like the little urbanites who cry wolf (or squirrel). But Squirrel Hill seems like a good fit here for the above reasons.
2) If public schools are not a concern and they would like something a bit more urban, perhaps South Side:
--urban and walkable
--I think there is a Giant Eagle
--walkable to South Side Works where there is a Joseph Beth bookstore and a movie theater
--restaurants all over the place
--a used book store on Carson St
--commute to California: 46 minutes according to googlemaps
--the trump card?: the 54C bus which goes South Side to the North Side via Oakland and "Bloomfield." There is a stop at Penn and Main which I think is about 3 blocks from the entrance to the St. Francis/new Children's site. Here's a link to the route map:
http://www.portauthority.org/PAAC/apps/maps/54C.gif
(even better for lostinpgh--the bus also goes to the Strip District)
[PS The Port Authority is indeed mainly set up for commuting from suburbs and city neighborhoods to downtown. However, there are a number of routes that go directly to Oakland--the "U" buses. And then there are these quirky routes that are not on any kind of hub and spoke-- 54C, 64A, 74A. Sometimes they don't run very often but they do allow one to get around the whole East End if one plans it out. Sounds like the OP is willing to do that.]