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I grew up in Portland but moved a couple of years ago. I'll try to answer...
>Cost of living?
Really depends on where you're coming from. The cost of living in Portland has risen drastically over the last ten years, specifically house prices. Where a house price of 130-150K was normal ten years ago, today house prices north of 250-300K seem the norm. However, if you can live (and work) in Vancouver, a suburb of Portland those prices are much better and do not have state income tax (if you work in Washington). Rent has been kind of crazy too. My boys college apartment that was $450 in 2002 is now renting for over 1K a month.
>Family life?
Great. There is so much to do. So many parks, neighborhoods and attractions. This seems to be the reason drawing people there. It is a great place to live, especially with kids. There is a lot to do, and it is easy to live there.
>Employment potential?
Employment can really suck. The engineering/architecture/construction field is however decent. Berkshire hathaway just bought Benson, an architecture firm locate in PDX. CH2M Hill has an office there as well. Jeld wen. The anti sprawl laws limit the growth (but helps the family life feature), which is a downside to this field. Vancouver (again in Washington across the river) is beginning a redevelopment of their waterfront which will bring in a lot of work in these fields.
As teefiveten stated Nike/Adidas/marketing (especially graphic design work) is a big field in the city for professionals. But there is a lot of niche jobs. It still isn't really great. I read awhile back that Portland has the most graduate degrees working service jobs. People come thinking they'll find work and don't but stay because they love the city. I guess that says something...
>Weather trends?
PROMO is right. Winter sucks everywhere. Except Florida, but then you're in Florida. Portland and the Northwest in general is pretty mild. Yes it is grey, but it is not cold as fuck. I've lived in Dallas for three years now, and honestly these have been the worst winters I have ever experienced. 80 one day then 20 the next. Portland is mild through the whole winter, and yes wet in the spring. It's mostly a drizzle, not a ATL style down poor. I never owned an umbrella in the 30 years I lived in PDX. A jacket with a hood did the trick.
>school me.
I love my city. I miss it every day. It is not the most diverse place, but I have never seen some flat out drop your jaw shit while living there. Gentrification has really hit some of the older neighborhoods. I do hate the idea that in order to redevelop that people were push out to the rockwall area and suburbs. But I guess that is Gentrification anywhere. Oregon does have a hell of a racist past, but all of America does. I would like to believe that doesn't include Portland today, but I have been told by friends that they sometimes feel like the only black face in the room.
If I could move back tomorrow I wouldn't even hesitate. As soon as my wife's residency we are likely packing up and getting out of Texas at the first opportunity, not because Texas is awful, just that we miss Portland so much.
Any questions I will try to answer. Just holler.
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