Yep, we all have to do things in our jobs sometimes that we don't agree with. Unfortunately this is how journalism is now, and its not unique to the Telegraph.
Think he's a musician (if it's the guy I'm thinking of), so quite probable he owns a local business or two. As you said, could also be that he's housing them temporarily (or someone known to him).
They found a heart condition during his medical so the transfer was delayed. He's had to have a 'procedure' to correct it. Suspect the Milan move will probably materialise for him again in the summer. Would imagine the fee would reduce a little if they are in administration and relegated.
Being a psychological/sociological thing and not physical, I'd assume that is where someone just wants to be considered as a person and not one or the other (in simplistic terms).
Just to point out (someone may have already done so), if your looking between your legs to check that's biological sex and not gender. Gender is a sociological term to describe traits, not physical attributes. Now, of you said you were cisgender male then that is gender.