The old balding drunk will probably be the most fun to play as in my opinion, i see alot of funny moments occurring with him in the main story missions also according to game informer, he is the only one who will probably be able to fly all of the planes and helicopters since he was a pilot in a war.
Surpass it in what way? Just being a GTA title doesn't automatically make it the end all, be all game of the universe. GTAIV is a great example. Being one of Rockstar's GTA entries didn't stop it from becoming one of the most overrated games (of its genre) to come out in years. Yes, V looks to be leaps and bounds better than IV, but that's not hard to do (see: GTASA).
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It's a fair bet not a single free roam on this generation will surpass GTA V. With that being said - come on. We've got the new consoles likely coming out in late 2013 so five years is saying a lot for that. I guess it's hard to say for sure, but with the new consoles very likely coming out about only a single year from now and five years being quite a long time we'll probably get something better whether it be from Rockstar or someone else.
If your opponent is of choleric temperament, seek to irritate him. --- In peace prepare for war, in war prepare for peace.