IMO, 8-ball is a terrible gambling game if one player needs a lot of weight. Games on the wire is probably the most fair way, but even that becomes unmanageable if the gap between the players is large enough (say, a C player versus an A player). Most spots involving balls are just hustles when you get down to it - the stronger player will try to give just enough weight so that the weaker play can clear some traffic before missing, giving the stronger player an easy runout. Unless you are fairly close in skill (or just trying to straight hustle someone), my recommendation is to play a different game, perhaps 10-ball, 14.1, or one pocket. All of those games are easy to handicap fairly.
Aaron