I think the biggest reason why they put most of the TLSQs in Y3 is because that's where a vast majority of the playerbase is at any given time.
People who don't cheat and don't spend money on the game are less likely to be in the later years and/or Beyond due to the exponential increase in energy requirements and attribute levels for skill checks/duels. Tends to chase away casual players from the game. They want as many players as possible to experience these TLSQs, and unless they're adding one that's specifically related to the dating mechanic, Jam City is almost guaranteed to stuff it somewhere in Y3, if not Y2 or Y4.