I've lived here most of my life.
Basically as Seth said we have a good transit system as long as you don't want to venture too far from the Portland Metro area. If you do there are buses to take you there, it just might take awhile. As with any mass transit system you will have to learn to deal with the tweekers and weirdos as well.
Weather is pretty cool. We seem to get 4 different seasons. Spring we have rain then sun then rain then sun. Summer is warm (but the humidity can get a little high some times) and the temp sticks around in the 80's with some days getting up higher. We seem to always have a couple of weeks in the upper 90's, but for most of the summer it is in the 80's. Fall is amazing. Still kind of warm and amazing colors. Winter is cold, wet and gray. Lots of rain and we do get a few days of snow.
As for stuff to do if you like the outdoors you will love it. Portland is an hour from a major ski resort one way and an hour the other way to the beach. There is also some of the best wind surfing in the world. Plenty of lakes and rivers for fishing and boating and a ton of trails for hiking/mountain biking. We have a good local music scene and some good art and a nice amount of independent movie theaters so you can see art house style movies if you are into that (of course a tone of other theaters as well for regular movies.) We also have one of the best book stores in the world.
The people are usually pretty cool but there are some areas of the city that are very "hip" and if you aren't into that scene they kind of look down on you. But otherwise I have found the people to be pretty cool. Sadly we do have a lot of meth heads and tweekers, but they are easy to avoid. We also have a larger than normal amount of mental people because Portland is very liberal (one of the most liberal cities in the nation) so we have a lot of programs to help disabled/mental/troubled people so they flock here.
Anyway, that is my take on the city. I love it here and don't have any desire to live anywhere else. It isn't for everyone though. It seems most people either love or hate it.
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