I think him getting 20 slams is more realistic than 100 titles.
Depends where his focus lies. His goal was to win Wimbledon again (check), get back to #1 (check), and win gold in the Olympics (TBC). Now that he has (pretty much) accomplished this, will his attention switch to chasing Connor's record of most titles won?
He spoke of this at the French Open (wanting to catch it), and he also said he plans to play until 2016 so, assuming his body holds up, it is within the realms of possibility.
Currently he sits on 75 titles, and Connors' record is 109. So to overtake it, he needs to win another 35 tournaments. Or, to be second on the list of most titles won (currently Lendl, on 94) he needs to win another 20.
Remember that next year (in his 31st year), none of the Masters tournaments are mandatory for him - so if he didn't care about his ranking so much, he could potentially play some of the smaller tournaments (with a much better chance of winning) in their place. Rome, Miami, Canada, Shanghai, Paris-Bercy are the tournaments he would be likely to discard from his schedule.
In 2014 he could, even, choose to play just
the smaller tournaments and the slams (I doubt he'll ever want to stop playing these until he retires). That way he could add titles from Chennai, Montpellier, Marseille, maybe Munich, Queens, Eastbourne, Newport, go back to Hamburg, play another home tournament in Gstaad, St. Petersburg, Thailand, Japan, Stockholm, etc.
If, for the next two years, he wins six or seven titles (say up to 90 by the end of 2014), then that would leave him with 20 more to get in his final two years in order to claim the all-time record.
That is just feasible, in my opinion, but only
if he drops the Masters and plays a lot more of the 250/500 tournaments. If he plans to keep a similar schedule to his current one for the next four years, then no way -- he must recognize that he will no longer (surely by his 33rd birthday) be able to compete at the very highest level, and therefore instead, go all-out in the lower tournaments if he wants to push his tally beyond Connor's.