The fact he has a fiance, in the area, was going to move in with her. I would think she would know where Gypsy is. I really do believe he loved his cat, especially due to his fingernails and his persona. I am sure his fiance is part of his life in a strong way since they are engaged. I would think she would have Gypsy or know where/what he did with Gypsy during his holiday for the wedding.
I am a hiker, camper and before I got old and fat (lol) I was a climber. I will tell you, if you try to push a vehicle at a trailhead alone, it can be impossible. The fact it was backed in, plate removed, and out of gas. I still feel strongly that it was run out of gas to keep warm. I looked at the evening temps in the area of Mount Hood and it was very cold in the thirties. (if windy could feel colder).
Job Corp people do not all come from Oklahoma. They come from many states. I remember one kid that was going there from Colorado, so it would not be unheard of for one from Oregon I suppose. My son had a friend that went to Job Corp in Utah also. So its not just a local thing. Job corp is mostly for troubled youth to be honest. Sometimes its court ordered. Other times its kids on the wrong track and its kind of a last stop before disaster, a hope of straightening them out and giving them a future. This is not from a website, this is from personal experience and the people I met while living in Guthrie that lived at Job Corp. I have also read that Job Corp may be closing down in Guthrie, and 250 young people have already been turned out and they are not accepting new people at this time. I wonder if any were being turned away around the time of the disappearance. I hope that the Guthrie police are checking with Job Corp. Also I know they have a curfew, so keeps bugging me why someone would be heading to town at that late hour. IMHO