Stay at the Ace Hotel and drink coffee from the in-house Stumptown Coffee Shop. There is a sweet lounge upstairs. WiFi all around, etc. Now, I respectfully do not recommend The Red and Black, unless you want a hard-core anarchist-collective experience. Really, you cannot leave Portland without hitting Stumptown coffee. Go to their website & hit all of the Stumptowns; that will give you a nice tour of various neighborhoods.
While on Belmont, go to the Blue Monk at night for live jazz. The Laurelthirst has good bands and good beer.
For a hip movie and dining experience, go to The Living Room Theatre (between The Ace Hotel and Powell’s) where you can eat, drink, and watch a movie.
The Doug Fir is a great place to see bands.
Portland is such a cool city. Talk to people that seem reasonable and they will point you in good directions. I have lived in the area for about 20 years and I never get tired of this great city.
Bottom line: Stumptown, Stumptown, Stumptown: http://stumptowncoffee.com/