You'd be surprised. A lot of the people on these "rich lists" are only there because they want to be. The journalists don't do a great deal of research (they supposedly check accounts and stuff but I know of at least one entrant who was worth F all and got rated as having a £25m fortune) and if...
He's converted a load of the loans into shares already and will probably convert more. As I said, he's not in this to get his money back.
I doubt there are any clubs that have made enough profit for the chairman to take £200m+ out. How much have the Glazers taken out of Man U over the years...
There was a really good article a while ago about why football economics makes absolutely no sense but is still sustainable. But I can't remember where it was or who wrote it so, er sorry.
The gist was that there will always be people willing to pay to watch football and there will always be...
I think he has said that he never expects (or needs) to be paid back. But yes, he deserves to not have to keep ploughing massive amounts of cash in and as you say, even one season in the top league would now mean that that would be the case.