Of the 125 largest cities in the USA, U.S. News and World Report recently ranked Portland as the #6 best place to live. This is a big jump from Portland's #32 ranking in 2017. The evaluators at US News describe Portland as innocent and shameless, quirky, friendly, offbeat and laid-back. The naked bike ride and Voodoo Doughnuts get top billing as examples of this, so "Keep Portland Weird" appears to be working.
It seems unlikely to me that US News' rankings and reviews are taken seriously by people considering a relocation. I expect that job opportunities and family connections far outpace some magazine rankings when deciding where to move. But people are coming, and as a California transplant that has now lived here for 15 years, I see the real estate evidence of Portland's popularity everywhere I go. Infill lots are gobbled up and new lots can't be created fast enough for builders. Rents are up, vacancies are down, and cranes dot the skyline.
But is it great being great? US News notes that housing costs here are higher than average and rising faster than in most metro areas around the country. However, we still offer lower housing costs than California or Seattle, making Portland a comparatively attractive real estate market for expats from those places. Still, with higher housing costs Portland self-selects out those who can't afford it, who are generally lesser skilled workers. As a result job growth and resulting development tends towards higher wage, higher skill work like tech and medicine, while employers who pay lower wages tend to look elsewhere. This results in a particular profile of commercial development, oriented towards offices and cleanrooms and away from heavy industry and outdoor work. This is probably good from an environmental perspective, but maybe a negative when it comes to ever-increasing traffic.
On the flipside, rapidly accelerating real estate costs are prime drivers of gentrification and declining diversity. Many vibrant communities lower on the economic scale find it harder to survive in their current locations and over time, may fade away. "Quirky" and "gentrified" are two concepts not often paired with each other, so what makes Portland great according to US News may also make Portland a victim of its own success.
As with most things in life, there are ups and downs, advantages and disadvantages. But I'd rather be in a "best place to live" than a "worst place to live." So yes, I'd say it's pretty great being great. The challenge is to figure out how to make sure our greatness now doesn't stop us from continuing to be great. So stay where you are and don't come here (just kidding)!