Not receiving the iCloud password reset email

Question

I am trying to assist a friend in retrieiving the information stored on his iCloud account via an iPhone that has since been broken
I've attempted to use the link several times to send an email to the Hotmail email address that is set-up as the iCloud user name but while I get the email sent confirmation, as yet no email has been received at this email address and I'm running out of suggestions as to how to help.
I also attempted to follow the security questions route to resetting the password but sadly failed at the first hurdle and I can only assume that his date of birth was originally entered incorrectly, as when I enter his actual birth date, I get an error message
I also thought that I might be able to access a password reset by using the same iCloud user name as his Apple ID, since with my own account, my Apple ID is the same as my iCloud user name but his iCloud user name is not recognised as an existing Apple ID
Any help or assistance would be most gratefully received as he's desperate to recover some photos etc that were uploaded to the iCloud from the broken iPhone  and with him being somewhat technically illiterate, I appear to be the only person who can assist and without the password reset email being received at the Hotmail address which is the iCloud user name, I am totally flummoxed as to being able to offer any further assistance.
With my utmost thanks in advance to anyone who might be able to offer any sugggestions or advice in this bothersome matter
Kind Regards
Bernard

Answer 1

Thanks a million randers4 for taking the trouble to get back to me.
I will get my pal to come over when we've both time to sit down and foillow your advice (and the link). However, sadly I suspect that we might have a problem proving his identity to the satisfaction of the support team, as whenever I've tried to assist this mate in the past, the same issues have always arisen, where he's not got a clue as to usernames, passwords, security questions.
I presume he must have some sort of underlying paranoia about revealing any genuine information about himself online. This proves incredibly frustrating and I invariably end up tearing what's left of my hair out, in my efforts to resolve his myriad of technical queries and yet while I invariaby end up losing patience, tired of trying to drum it into him to write login details down, to keep them safe, or to only use answers that he knows he will remember, in light of everything that's come to light recently, in truth perhaps it's me who is the stupid one for freely giving up all my personal information online and it will eventually prove that he is most sensible for refusing to relinquish any genuine personal details about himself.
Then again, at least I am able to retrieve my iCloud photos!
Apologies for waffling on. Hopefully I can come back to say issue has been resolved, but I've an inkling I might have to return to enquire if there are any further options
Kind Regards
Bernard