Portland is a great city, bike friendly good size etc. Many Portland members here on this site will give you more insight. A little too much indie attitude perhaps, but Seattle has its share of that as well. As for fenders, I'd say yes, if you are going ride in Spring, fall or winter. I commuted for years without them and once I added them, I no longer skipped the rainy days. Essential in my mind. However as much as it rains here, it is often drizzle, and the summer often brings 3 months of little rain.

Anyway I'm off to do a little snow riding myself