Thank you very much for your explanation. This has a lot of ramifications and I will be sure to advise him on that and,... I agree with your points. 

If he was your client, for year 2022, would you deduct any of the mentorship expense which allows him to contact/consult with experts and which he pays monthly?   Would you deduct any of the renewal of the coaching program?  or would you classify those two as non deductible just like the original course he took.

Thank you in advance for your answer,