So call me behind on this reply....
But I think in the case of the young, prototypical "rockstar" (like John Mayer) you have to play the odds. Yes, a cougar can and will bang your brains out in an experienced fashion, but I believe that you have to work harder and there is less opportunity out there if you're going for an experienced experience. Cougars may play harder to get, and there are less of them out there comparitively speaking.
However, if you go the other way, you have hordes of young girls just waiting for you to ask them to blow you and/or give up the poonanny. Therefore, you may not have as good of sex all the time, but because of the sheer number of times you have sex with the younger lot, you will end up having more good experiences than bad (after all...as long as you busted one, it couldn't have been that bad, right?)
So he should drop Anniston and go forth and have sex with as many youngins as possible.