We went on a Tuesday to a Tuesday this past October because airfare was cheaper to leave in the middle of the week.
We stayed at POR, arrived around noon, waited 20 minutes to check in (which seemed a long time when there were only 3 people ahead of us but that was because of a major computer problem that day) and our room was ready. Check out was less than 10 minutes @ 10AM +/- and we did not have any wait to check our bags with the airline desk at the resort.
Hope this helps!