If he went to a boarding school and knows how to advocate for himself then he will do just about at any college. Most students really don’t have the art of self advocating when they start freshman year. He’s already ahead. There really isn’t alot of hand holding at college. You need to ask for the help but there will be plenty like peer to peer and professor hours type of help. I personally wouldn’t worry about him at Wisconsin. Also regardless where he went to school college tends to be harder. After the first few weeks he will understsmd what is expected of him. Many, many students do fall behind in the first few weeks due to the different work loads in college. As long as he knows that he will be fine. There is always the work hard /play hard mentality many colleges have. Good luck.