I'd also have to ask WHY he wants the item? Did he dump his lowest stat into charisma? Did he beat up some old lady for not revealing information, did he do unglorious deeds and now he wants to take leadership at 6th level but because of his penalties he can't get a cohort of anything higher then 4th level so he wants an item that adds a bonus to make up for the way he roleplays his character? Tough luck I say!!
Was he made the leader of the Kings forces due to unswerving bravery in the line of duty but even though he has tons of bonus's for being Kind and friendly, and fair, and generous, etc it still isn't high enough for the flavor and he needs a bonus in order to have the amounts of followers that you think his position deserves? Then I'd say he gets an additional +2 or +4 or whatever for the direct endorsement from the King, but please don't make it into an item that you can buy in order to make up for not being a kind and friendly person (character).