Which commute would be least painful? (Pittsburgh, Mount Lebanon: homes, neighborhoods, to live)

[exp]

Beginning next year I’m going to be starting a new job on Highland Drive just east of Highland Park. I'll try inserting a link to a map of the location (it doesn't seem to work, though): Highland Dr, Pittsburgh

Unfortunately while a commute from north of the Allegheny river would be ideal I need to live south of Pittsburgh to be closer to where my wife works. This could be anywhere from the southwest (Cecil, North Strabane) to the southeast (North Huntingdon, Irwin) and everything in between (Mount Lebanon, USC, Peters Township, etc.).

From what I've heard this will be a pretty bad commute, so if there's any way to minimize the suffering it would certainly affect which neighborhoods my wife and I look into.

I’ve been looking over maps of the area and there seems to be three main ways to approach Highland Park from the south. Since I’m not familiar with the area and just plucked these routes off of a map I realize some of them might be ridiculous or even impossible. That’s why I could use some inside information. What would these commutes be like? Are any of them potentially easier/shorter than others?

Option 1 (from the southwest): Take Route 28 east in order to cross over the Highland Park Bridge from the north. In order to even get onto 28 in the first place I would need to use some combination of I-79, I-279, Route 19, and/or Route 51, and then choose one of several river crossings:
....1a) Take the West End Bridge.
....1b) Take I-279 through the Fort Pitt tunnels.
....1c) Take the Liberty Bridge and I-579.

Option 2 (from the south): Follow the Blue Belt through Squirrel Hill. This would be the most direct route, but also one dependent on much smaller roads. There are a couple of bridges I could use to cross the Mon into the vicinity of Squirrel Hill:
....2a) Take Route 885 to the Glenwood Bridge and then cut east to connect to the Blue Belt.
....2b) Follow the Blue Belt directly over the Homestead Bridge.

Option 3 (from the southeast): Avoid river crossings altogether by driving in from the southeast. At least the Highland Park location would probably allow me to avoid the Squirrel Hill tunnels. My choices here would include:
....3a) Take Route 30 northwest into Wilkinsburg/Homewood to connect to Penn Avenue/Route 8.
....3b) Leave Route 30 early to take Route 130 north to the Allegheny River where it turns west toward Highland Park.
....3c) Take I-76 north to at least Leechburg Road before turning west, thereby avoiding Route 30 altogether. This would be the furthest route in terms of mileage traveled, but could it possibly be faster?

Thanks so much for any help!

[LadyOfTheLake]

If you're going to be out in the North Huntington/Irwin area, your best bet is to take the turnpike west and get off at Allegheny Valley--near Harmarville. Then take 28 South from there.