I play many games, but there are only 2 that I play every update (from the beginning). Usually, I wait for 3-4 updates before replaying a game. :
College Daze : a lot of replayability. A "simple" (for the player at least) but interesting game system. A LOT of choices leading to different paths. I play it entirely at least 3 times per update.
Photo Hunt : A sandbox game with a lot of content, with branching routes for the endgame of some of the girls
There are other great games, but I don't replay them that much because they're either too linear (like the Timestamps series, really worth playing, but no replayability) or have too little content.
