Having commuted in Portland for over 25 years, here's my advice: any lugged steel frame (and some good aluminum frames such as Cannondale) with a touring or sport touring geometry (stretched out) from the 80's of reasonable quality will be incredibly fast and easy to ride and to maintain. Make sure they have eyelets and brazeons for fenders, racks and bottle cages. Make sure you get alloy wheels which are lighter and safer in the rain. These bikes are bullet proof, and anyone with basic mechanical knowledge can do most of the maintenance. Consider: Centurion, Miyata, Peugeot (also with internally brazed steel frames), Trek, Motobecane, Bridgestone, Novara, Nishiki, Specialized,etc. You will spend virtually no money on these bikes and can add moustache bars, or any other accessories for that classic look and still put $500 into your savings account. While the older classic touring bikes are gorgeous (Raleighs, etc.), they weigh in at 40-50 lbs, have steel wheels and only 3 speeds. This is fine for flat roads with cobblestones, but not for the fast, hilly, wet commute you do in Portland. The newer bikes that you listed are really not of the same quality and will be more expensive to maintain than the bikes listed above, plus they are more expensive because you are buying a new bike. And, you'll lose tons on resale value. So, consider a used bike!!!
