i personally am not a fan of his videos.. but they do seem to be very popular amongst majority of fans.. and somekind of official vids from him for the club may make some money for both parties... behind the scenes kind of stuff.
youtube videos can be big big money if done right. so could be something of a collaberation for the club
as for the TV rights.. yes the TV companies etc and League suck. but they pay millions for their rights to own footage so cant really blame em.. as for all of us in our lives every penny counts.