WOW, cyccommute, there’s a lot to chew on there, thanks.
As far as the shorts, He and I, as most adults and young males are not proportionally the same. The chaffing I felt was due to excess movement, which he probably does not suffer from. I cannot ride one mile without my tight fitting shorts, I also have some fox mtb shorts that are fine. He on the other hand has done 10-15 miles in jeans and sneakers without a complaint, as did I as a kid. The Fox shorts are pricey, I'm sure there are other brands that are just as good. I'll try him in something other than the ems shorts, something a little tighter.
He already wears wicking type t-shirts when we cycle, hike, or just as a regular shirt.
Like I said, after a few long day rides and an overnight, I'll revise the mileage, and route if needed.
I didn't think of the bar ends, but I do have some and will put them on, thanks. I have thought of the camel back myself, I wouldn't like it, but I'll try him with it. I had not thought about the front rack, if I can find a cheap one that will fit his susp forks I'll pick one up. I originally was only going to have him carry his sleeping bag, but funds are low and I cannot afford larger front panniers, and I saw some cheap ones on nashbar - $39, I thought they would be perfect for him.
Yes, Yes, Yes on the journal!
Jon