An observation I've also had is that not many people factor in time, maintenance and repair costs when considering Portland homes. I've looked at $350k houses here that are complete junk without another $50-200k in (I'm not just talking kitchen remodels, just as often I see serious roof and water damage problems), and therefore really are priced at $450-600k. Real estate brokers have been.. less than stellar about disclosing some of these issues to buyers. One place I looked at was listed at $375k, went for over $450k and had in the house, no shit, uninsulated knob-and-tube wiring going into a fusebox model from the 60s that was recalled 25 years ago for electrical issues. Better to get your Will settled before moving in there.
When you factor in these hidden costs, things start to look very overpriced around here. I expect that in the next five years there will be a lot of disgruntled owners putting these houses back up at purchase price (or maybe even less) after they get sick of dealing with the problems and start to realize the price tag to fix them.
In the interim, the bad news is that Portland is basically out of housing stock at this point too. Expect more rentals and condos in the future.