Here's another analysis, from someone who has lived in the Portland area almost all his life.
Another interesting survey shows that Portland is one of the most depressed cities in the nation - depressed, as in sad and gloomy, not economically. Maybe it's that Portlanders are so accustomed to what we have, that we don't bother fighting for something better. Sure we take a good idea from elsewhere (i.e. light rail, bike paths - two things we certainly did not invent, but they're something we do a lot of), but when we screw something up we don't bother complaining about it. We just accept mediocrity and plan our lives around it.
Portlanders that move - yes, they move to a better place. But when it's sunny and warm you have certain expectations. No, Los Angeles is not a resort city. New York is jammed full of people. Europe costs sky high. Meanwhile, folks who move to Portland find a lack of jobs, it rains a lot, it's hard to get places (despite Portland's assertion that you can live without a car - it's possible, but it is in Los Angeles, Houston and Atlanta, too.) Yes, Portland is close to the beach and the mountains and the Columbia River, but not everyone surfs and skis. If you have a great job here and enjoy the nature, I'm sure Portland is a great city for you and that's OK.
Another reason we don't complain much is because of apathy. How many people in East Portland bother to vote? How many of them voted last year for President, and how many voted for Mayor? (A lot fewer participated in the Mayoral race.) Many people are just tired of the divisiveness in our local decision making, where a small minority of folks have a huge voice, while the majority of residents are ignored. The per-capita income in Portland is less than $30,000; yet you wouldn't know it by our housing and development plans that frequently ignore the average Portlander, but spend a great amount of detail to attracting well-to-do outsiders to live in the Pearl and SoWa. There are only 136,259 owner-occupied homes in Portland, and another 100,000 rental properties -- that's a full 10% more rental properties in Portland than the U.S. average. We have a school district that is one of the worst - there's a reason families are fleeing for Washington County, where the Beaverton and Hillsboro school districts have been growing and building new facilities at the same time Portland is shutting down and consolidating schools. And when the public tries to speak - the school board shuts the public up.
Our transit system is a perfect example: if you're a Streetcar rider, you are considered a "choice rider" by TriMet. But if you're a bus rider, you get socked with service cuts, poor service, an aging bus fleet...it's the perfect example of "separate but equal". Yet...TriMet's board is unelected and few have the time to be able to attend a TriMet board meeting (one of the few actually scheduled during working hours, instead of the evening hours when the public is more capable of attending).
Portland has its good points, and its bad points too. Portland is not the greatest city - I don't know what is. It depends on what you are looking for; what's great to one person is not to another. I grew up here, my family is here, my roots are here - that's why I'm here.