My veiled chameleon (edgar) used to go near her favorite branch in the morning and wait there until i fed her. She would'nt budge from that spot on days i didn't feed her (I fed her every other day).
Could be he is trying to rub the skin on his tail and feet off. I can imagine shedding your skin is somewhat itchy. You husbandry seems fine. Maybe some more experienced keepers should chime in.
I casted my vote as no originally ( i thought you mean't emotional support like him being with you everywhere) but I guess you should cast him as emotional support if you want to keep him on campus. I would have trouble just giving away my beloved pet.
If on the right gutload probably, but many types of caterpillar are picky with their food and will only each that specific food and, in many cases the plants are poisonous and that poison sticks with them their whole lives. We have lots of these in my area and i've never gotten them to eat...
I would suggest more females in general. I kept a a hissing roach colony and a dubia roach colony and to get more I would mostly just increase on females. Don't expect them to start breeding a bunch of babies in the beginning. for the first couple of months i still purchased dubias for my cham...