I'm not fussed, but it does annoy me when he doesn't wear a suit on match days, but I think that's a personal thing.
Jimmy was referencing a song. We used to sing songs at Spurs back then.
Big Martin was ace. He seemed like the kind of bloke you'd love to go out on the piss with. I think the players seemed to love him too.
You're correct that he was shit at tactics but the football entertainment was brilliant.
I know it's a cliché but results aren't everything. When we had Berbatov, Keane and Lennon taking the piss and playing the game* for the right reasons -- fun and enjoyment -- it was fucking immense.
*we often forget that that's what it is. It's a game, to be a source of enjoyment, not a cure for cancer or third world poverty. (I hate the famous Shankly quote. I wonder what his mrs and kids thought of that bollocks.)
Tl;dr Jol felt like one of us.