I think last season's final handicap table goes to show just how hard it is to win such a bet. City (in terms of points and league position) finished well ahead of where the bookies, the pundits and most fans expected they would before the season began, but they were still nowhere near landing the handicap bet - some 23 points short, in fact.
I was surprised to see Sunderland are only 3rd in this years table so far, Assumed they would be well clear but like you say it only takes 1 other less fancied club to have a half decent season.