If I were me and were going to Portland for the first time, on a limited time, I'd for sure want to stay at McMenamin's "Kennedy School"...:
http://www.mcmenamins.com/427-kennedy-school-home
...why?
- The place is the coolest hotel you'll ever stay in. Well, OK, maybe quirkiest...
...but, in a good way.
- Prices are very reasonable for the room.
- They have a cigar room, on site.
- They have a micro brewery, on site. Their beer is quite tasty..!!
- They have a couple of different places to eat, on site.
- They are right on the bus line, so getting downtown or transfering to Max, etc. is a snap.
- It's about 20 mins. away from my house across the river in Vancouver, WA so I could come by for a smoke...

Food for thought - B.B.S.