Thank you everyone for your thoughtful and supportive comments and advice. I will be sticking to my professional responsibilities on this matter and using your suggestions to be as fair and accurate as possible. I still have until October to try and help him as I feel the need to give extra efforts, not so much that he is a friend, I would do this for anyone. What is at stake is a 6 figure amount with a 3 in front, so this is serious, as is any other tax return.
I read this thread before bed last night and must report to you that because of all you said I slept well, no tax nightmares. You should all have RTST after your names, Registered Tax Sleep Therapist. Thank you.
Grateful in MA,
Bill