San Francisco has the best weather of any of the more popular cities; although when it rains it really fooking rains. The funny thing is Californias turn into sugar when it's wet; instant pudding, total wussies, so if you don't mind rain you have a big advantage, and the rainy season is only 1 to 2 months long. Portland is the emerging hipster/artist/vegetarian capitalist/trendy/progressive city and there are scores of fixies, sspeeds and just bicycles on the road. There is no traffic anywhere compared to NYC, Oregon may put you to sleep. If you are riding for a living don't look to the west coast, I don't know about Seattle but most messengers don't make much compared to Chicago, Boston or NYC messengers. I don't know about Minneapolis. In SF I made 100 a day on average and that's lousy pay when rent is 500 plus bills and temps make 15 an hour under the table. Although if you dedicate 5 years to one company you are bound to make twice that a day. And Portland messengers make hourly, yeesh.