Hey Melissa -
Portland Native - lived here all my 42 years besides college days...
In GENERAL - and this is way, way general, so other Portlanders don't jump down my throat...
Westside is newer - the most affluent part of the city is probably NW, though there are parts of NE and SW that are pretty spectacular, too. SW is probably the most "suburban" part of the city. NE is old neighborhood Portland - the neighborhoods can be a bit patchy, but in general they're smaller houses in tidy neighborhoods. North Portland can be pretty run down (as well as inner NE and large chunks of SE).
In case you hadn't gathered already, Portland is in 5 sections - N, NE, SE, SW, and NW. The Willamette river divides the city E/W and Burnside St. divides the city N/S. North Portland is North of a curve in the river and lies between the river and Williams Ave.
I don't have much bad to say about Portland. It's kind of a goofy place at times, with the city's unofficial motto being "Keep Portland Weird." If you've seen the Independent Film Channel's "Portlandia" you get a feel for the weirdness - greatly exaggerated, of course. If you watch the opening sequence, I've actually seen several of the weird things they depict just while driving to work in the morning.
It's a good city for cyclists - pretty bike friendly.
There's recreation of just about every kind nearby - year-round skiing, watersports on the Columbia river, fishing, camping, mountain biking, the beach - a little bit of everything is available within a 60 mile radius. I think we're the only major U.S. city to be within 60 miles of an active volcano...
Don't overlook Vancouver, Washington, either. It's just on the other side of the Willamette from Portland and is part of the metropolitan area. I don't know Vancouver very well, but I've heard it's less expensive to live there (not that Portland is an outrageously expensive city...). Keep in mind if you consider Vancouver that if you work in Portland you WILL pay income tax to Oregon. Washington has a sales tax, Oregon does not. You can pump your own gas in Washington - it's illegal in Oregon (go figure...). You will forever be irritated by cocky Portlanders who make jokes about "annexing Vancouver' or saying "Vancouver is really just a part of Portland." I guess you're Canadian, though, so you've probably heard plenty of "51st state" jokes...
Anyway...PM me if you have any other questions or want a more down-and-dirty description of parts of the city...
