Well, I can give some perspective. My grandparents lived in New Kensington from the 50s to the 90s. We lived in the South Hills.

As the link provided said, there was nothing on the North Side, no links to anything. "28" was no different to 19 in the South Hills, just a label applied to existing local neighborhood roads.

If we wanted to head up, I remember two routes. First, taking the parkway to Monroeville and cutting via back routes to Oakmont to Freeport Road. Second, cutting through the city to Washington Boulevard and taking Allegheny River Boulevard to Oakmont, then cutting across the Allegheny to Freeport Road. Both sucked, especially during rush hour.

Fox Chapel felt less connected than Sewickley, for example.

IIRC, it was well into the 80s before we started using 28. Until some point, you still had to drive around the Heinz plant. Obviously, 279 was a game changer as it started to connect the various major roads. However, with the churches and the rail lines and the existing bridges at 31st and 40th, I never imagined it would ever be like it is now.

Yes, the Highland Bridge Interchange sucks for now. But, when it is finished, it's going to be a route Pittsburghers never could've dreamed of. I don't want to sound booster-ish, but this is one project that has truly changed the local geography.