No matter what advice you give him there is probably a 80-90% chance he will be rejected. Based upon what you stated he is (reaching out of his league). "I believe his main attribute is his kind and honest heart." That is not the kind of thing (most) girls and young women make a (top a priority) when it comes to finding a guy. In fact if the girl he is interested in wasn't "gorgeous" would he be dying to ask her out??? Is (he) looking for a girl with an "honest heart"???
Generally speaking like attracts like and water seeks it's own level. A large part of being young is being shallow. It is not until after most people have matured or have had their heart broken a few times that they start to make traits other than good looks, personalilty, and finances a priority. There is a big difference between boyfriend material and husband material.
Having said that my mother use to tell me: "If it ain't worth asking for then it's not worth having." One thing is for certain if he only asks "gorgeous girls" out he'll face a lot of rejection but when he does find a girl who wants to be with him she will be "gorgeous". Successful people get rejected more than unsuccessful people because they keep going after their dreams!