Hate to say it, but with the timing and the 3*+ range there's some danger of running up against the prom crowd. Don't say you weren't warned.

I used to be a frequent 2* bidder, going after $30s. Years ago the Doubletree Lloyd Center was doable for that through PL, but not lately. Once got the Inn at the Convention Center in same neighborhood...good location and no parking costs, but a little tired.

Probably the best luck has been with the Extended Stay Americas in Gresham and Vancouver (the one in Hillsboro is just too far out). Very good value if you can do without maid service every day.

As for food, Jake's Famous Crawfish downtown is a must (the Oregon 3-berry cobbler for dessert a la mode is really great). The Sunday brunch seafood buffet at Salty's on the Columbia also was great (reservations really help, as does a big appetite). Hands down the best steak value is the Acropolis, but it's not that family-friendly.

Definitely go see the Gorge and Multnomah Falls. The drive around Mt. Hood can be pretty as well.