OP, we arrived betwen 1 and 2am to POR on our last trip, and except for pretty much having to scrounge up a Bell Services guy and deal with the silliness of the messed up online checkin stuff (we had booked through hotels.com and even though I was able to link the reservation they didn't have the names for DH and DS, my CC info hadn't come through for room charging, etc), it was fine.
We got exactly the sort of room we had booked and wanted.
It is sometimes hard to pay for a room you'll barely be in that hotel-day, but when you wake up and you don't need to move, or when you don't have to spend a few hours in the lobby waiting for it to be the hotel-day that you booked, it's fabulous and can feel well worth it.