Thanks for the help, everyone!
I was finally able to find a suitable combination of scheduling and weather and made the trip. My work friend and his wife were able to come along for the ride. In the Willamette valley we had scattered clouds at about 3000', so we were able to pop up through the layer and start flying direct. Enroute, we climbed in steps from 7500' to 9500' and a short stint at 11500'. The mountains were absolutely beautiful. We flew right over Toketee State airport and near Diamond Lake before reaching Crater Late. The rim was still almost completely covered in snow.
Once past Crater Lake, we had to dump a few thousand feet of altitude for the 5500' TPA at Chiloquin. The first landing pass was way high, so I went around for another. The ride down was very turbulent and bumpy. I was working hard to stay lined up and stable. Our lunch at Melita's was delicious, and is clearly the local eatery.
When we were getting ready to take off again, I was giving the plane a quick preflight (including a fuel check). We use those clear sample tubes that are calibrated in gallons. When I was getting my finger ready to put on the top of the tube, it slipped out of my hand! The tube fell onto the side of the gas tank opening and agonizingly slowly fell into the tank. After muttering some choice words, I started thinking about what I could do. First, I thought to call the maintenance manager for the club. Voicemail. Next, I called the FBO, the suggestion? Try to fish it out with a coat hanger. Luckily, there's a motel across the street, so I found on easily. After almost an hour of fishing and cursing, I call back. This time I ask "Is it safe to fly with the damn thing in there?" The mechanic said that it was, but that we would have to put the plane down for maintenance when I got back (to get it out).
The flight back was a bit more stressful than the one back, I'll tell you that. In large part because there was a strong head wind at 10500'. I was only showing 78kts GS on the GPS. As soon as I was past the Crater Lake wilderness area, I dropped down to 8500' and started getting 105kts GS. That made me feel so much better. By the time I got back to the valley, the clouds were few at 5000'. Landing at corvallis was entirely uneventful. Overall, a great trip!

More photos:
http://www.flickr.com/photos/28728868@N06/tags/craterlate/