I think your trip looks awesome. I moved from Chicago back home to Oregon and did much of the same thing just headed west thought. We drove to the badlands in one day and then drove out of there, hit Mt. Rushmore, and all the way to Cody, Wy. all in one day made for a long day but then it would...
I have really like the exofficio boxer briefs from REI. That and a sent free powder will help. I have used the body glide with triathlons and that works really well for them so I would imagine it would help for hiking as well. I just have not tried that.
The thing to think about is how the people who have the once in a lifetime tag would like to have someone come up on a buck they were stalking on and mess up their hunt for a picture.
That’s a tough one. With a ton of debt from school that is on your mind if you can’t pay that can make your move more stressful if you go. That can decrease how happy your are moving vs being comfortable and taking trips out west.