I can understand your delimma, have you talked to the school counselor? what about a psychologist?? I dont know what I would do, probably instinct is at this early stage in their schooling I would say keep am all down, for his esteem issues, as esteem is really as important as education, and its not like they are in yr 12 ( IYKWIM)
Have you contacted AMBA in your area? coz I know they have lots of books and a special support group for mulitples in school. Welcome to BB, and look forward to hearing from you