Designed and written for the DIY-inclined person without any cash to spare, the Zinester's Guide to Portland breaks down the PDX grid by neighborhood with descriptions of good restaurants, thrift stores, bars, bridges, places to loiter, etc. (lots of etc.). The newly overhauled and illustrated sixth edition gets shoulder-deep into the history and local lore, providing a well-rounded argument as to why (fill in the blank) deserves your time.
It also demystifies the TriMet public transportation system, bike events and culture, outdoorsy stuff, the public libraries basically anything...