Here's my post to someone else who was vacationing in Portland from
this thread.
"Hope it's not too late, but here's my 0.02...
1) Depends on who you ask. There's definitely an east side/west side divide (the Willamette river). North Portland is known for gang activity, SE is kinda known for it's drug issues. West side is nice, but kinda removed from all the fun, touristy, fun Portland stuff. Like the other posters said, I'd stay near the MAX tracks in downtown. DO NOT stay on MLK or near it!
If nothing else, Portland definitely has a drinker friendly night vibe going. Hell, they even shut down a few square blocks on the weekends to traffic to drunk people won't get hit by cars while jaywalking...true story. My favorites are Barrel room and if you want the definition of a dive bar...Yamhill Pub (there's a broomstick in the bathroom to be used as a lock).
2) All the Simpsons characters were named after downtown Portland streets...that should give you a clue. Nob hill, Pearl District, and the Waterfront are all must sees. Chinatown is kinda janky. Mills end park (look it up), Pioneer Courthouse Square, Pittock Mansion, Rose garden, Portland underground tour (starts at Hobo's bar) is neat, and all the Portland fountains are way cool.
3) Yuki's in Nob Hill is good and so is Mio Sushi, but I'm not a Portland sushi aficionado.
4) Medford has GROWN! When my wife and I made the same trip to SF, we stayed at the Rouge Regency in their Presidential suite. It was surprisingly affordable and they have a great sports bar with comedy shows on the weekends attached to the hotel.
hope this helped,
HAVE FUN!"
Furthermore, Deschutes, Full Sail, and Rouge live here. They would be sad if you didn't stop in for a visit. You can't swing a dead cat around hear without hitting a micro brewery either, so no worries there. Don't make eye-contact with the homeless people. They're fuggin' A-holes.
Henry's tavern is also a must do. It's the old Blitz-Weinhard brewery that they turned into a cool bar/restaurant (Gorgonzola cheese fries...hint, hint).