Cleveland: The favored quarter is definitely, although perhaps unexpectedly, the east. This was always the old money part of town with the ornate gilded age mansions. The Heights are the suburban extension of this, complete with their own century old mansions. What is strange about this is that the Southeast and Northeast are the least favored quarters, and that the east side of the city of Cleveland proper is in pretty unfortunate shape these days, so it may mask the fact that the east side is the favored quarter. The remains of the favored quarter are now something more like a wedge between the poorest parts of the city. The west side, which has the reputation of having more stable neighborhoods, was always a working class part of town and mostly remains a stable working class area, albeit with some gentrification in the inner and lakefront areas.
Claire Malone describes the West-East divide beautifully in A Tale of Two Suburbs
Portland: The favored quarter is the southwest, although there are favored patches on all sides of the city. But the West Hills provides such a clear natural advantage to the West that this should be pretty predictable. The least favored quarter historically has been the north, but the north is slowly being gentrified and the far southeast is declining.
You could say Portland’s favorite quarter extends into Lake Oswego, and arguably across the West Hills into unincorporated Washington County within the urban growth boundary. I can anecdotally second your observations about North Portland and the far Southeast, although most of the stories I hear about SE Portland have to do with the more gentrfied/whiter inner part, west of 82nd Ave.
Parma is on the South side, The western suburbs include Rocky River/ Lakewood which are also relatively UMC and upscale although its more of a new-money type.
There are definitely some upper middle class suburbs on both sides of the city, though Lakewood is more mixed than really upper class. No one really uses the phrase "South Side" except to describe Tremont itself (which is simultaneously consider to be on the Near West Side), or perhaps the Cuyahoga Valley. Cleveland is very East/West centric.
What I discovered about Cleveland while "enjoying" the hospitality of the Cleveland Heart Clinic for 40 days, is that the topography around the Cuyahoga River is really picturesque, and the money follows it, all the way down to "Hudson" in Summit County. Why was Hudson a wealth pocket I always wondered. Now I know. In LA, air quality caused the eastern suburbs to lose cachet for the west side, and when air quality improved, the east side wealth suburbs came roaring back with a vengeance, with the Chinese now displacing the WASPS en masse.
