i dont know much about the questions you asked but i can tell you a quite things.
if you are working in a corporate or multinational company than 16 years of exp and all that will be counted first. after that any preferable tool you have in-hand will be appreciated. like digital marketing course.
incase if you are applying for digital market job to phr apka job experience kam nahi ayega, because job requirement kuch hai aur apka exp kuch.
in my opinion their is not any problem, while it may be personal criteria of employer for the candidate appearance. a candidate selection should be on basis of his qualification and experience and other requirements rather than personal selection criteria.