Just read this from someone who has been looking at this subject for years.
Absolute worst, hands down, Homewood and all wards in a 5 mi radius (other than if you cross over Penn into Point Breeze). Just listen to the news. That being said, that isn't too far from East Liberty which is starting to get gentrified. But as you can imagine you get spill-over. Just like someone mentioned about getting their car taken in Friendship... Go figure, it's 2 mi. Away from Garfield.
Next crappiest: Hill District, even though it's kind of emptying out... Sort of vacant, but historically the worst part of Pittsburgh.
3rd crappiest: entire Northside behind central Northside. I hesitate to say that because I'm covering a lot of area with this statement, but in general.
4th tier: just in total decline with some crime; Mt. Washington (South) it gets worse and worse the further off Grandview ave that you go then you hit: Allentown, beltzhoover, Knoxville, Southside slopes sucks too., hazel wood can be put in this category too and far north Northside (Brighton Heights, Perry North)
5th tier: just in decline... For sure just to get crappier or stay crappy: west end, sheraden, esplen... Swissvale looks ok but seems to be heading in tge wrong direction. Troy hill too
Nicest areas? Squirrel Hill (north of Forbes), shadyside. Super nice areas but thanks to the over abundance of crappy people in crapiy areas you always hear about bank robberies in SH and assaults on Shadyside.
Want something different (or even a big house) in a ok area? Highland park, allegheny west, Southside if you are young (but annoying because if the bar scene), Lawrenceville if you like a little more quiet, Mt. Washington (close to Grandview) seems to have a lot of 20 something young professionals
No comment: Bloomfield (seems ok?), Stanton heights (never hear anything good or bad... Don't really know). Oakland is just college kids
Outside if the city:
Stay the hell away from: Wilkinsburg, McKeesport, Duquesne, Braddock
Getting crappy: penn hills, McKees Rocks, n versailles, carrick
Nothing bad reported but I wouldn't invest my $ (people will prob disagree, just my observation) Crafton, Coraopolis (old part), Carnegie, lower Ross Park, Avalon/bellvue (along 65), Millville, parts of Monroeville, West Mifflin, forest hills and Churchill (once really nice... And still cute and maintained, but hit my the merger into the crap woodland hills school district)
Good investment (not so expensive...young families) Brookline, mt pleasant, dormont, whitehall, moon two/Robinson, glenshaw, north huntingdon, plum, aspinwall, Ohio twp, Chartiers/Bridgeville
Nice: mt Lebanon, entire north hills and Hampton ( can get some good deals, most really nice) moon, murrysville, Sewickley area, upper st Clair, Fox chapel