A little feedback and advice following my trip. Indeed, kudos to Les Schwab in Sandy, OR for buying chains. Cost me $35 for the chains and they offered to take them back for a full refund if I didn't need them. Really good and friendly customer service. I was in and out in 5 minutes. Well, I ended up needing the chains and it was no joke. My advice if it's puking and you don't have chains, don't attempt the drive to Mt. Hood. They do not salt the roads so you will be driving on several inches of packed snow/ice. The plows push some of the snow off the ground, but the snow is so wet that it quickly forms a heavy crust on the road. If you've ever driven on untreated dirt roads in New England, that's what you are in for. I didn't see any checkpoints even though chains were required so you could take your chances, but, again, I really wouldn't recommend it. Getting chains on your car the first time is a pain, especially the cheap model, which is not very user friendly and limits your speed to 30 miles/hour. (Most locals have studded tires and drive regular speed so you infuriate quite a few people.) Don't forget some light waterproof gloves to get the chains on (ski gloves won't cut it.) Made for a memorable experience. It's too bad that Mt. Hood doesn't offer a regular shuttle in these conditions as I can imagine this ordeal is quite a turn-off to most tourists. Mt. Hood is rather convenient to the airport, but it took me a good 3 1/2 hours to rent a car, get chains, outfit the car, and drive 35 miles at 30 miles/hour. Utah makes it so much easier. I seem to remember shuttles from the airport and the Utah Transport Authority offers a lot of cheap options as well from downtown or from the park and ride lots at the entrances to little or big cottonwood canyons.
That said, if you make it to Mt. Hood Meadows, you are in for a treat! Great mountain with a lot of diversity for all levels. Had a blast!