Welcome to Havana on the Willamette. Yes, as Barman noted, I currently reside in Portland.
Hawthorne is a happening place with all sorts of bars, restaurants, shops and a sorted bunch of patchoulee-wearing flotsam and jetsam drifting about. A few people in that area are regular 9-5ers. You will also come across a large segment of lesbians ( and not of the lipstick variety) in the Hawthorne district.
My favorite cheap eats is a place down on 35th. It's a mexican place called Cha cha cha. Decent cheap food. The only other place I venture to on Hawthorne is the supermarket called Fred Meyer. It is by far the best supermarket, but also very Hawthorn-ish. They have a great deli/food to go area. And if you like beer, you will be hard pressed to find another place with a more extensive selection.
Portland excels at a few things a young guy might like: coffee, beer, weed, and strip clubs. I guess the live music scene is pretty good, but I can't tell you anything about that.
If you have specific questions, ask away or send me a pm.