Using Cayenne as an example she is "introduced" to the MC by Daisy as a special saturday project to visit if I remember correctly. Those early events did trigger even though the story was significantly past those points and without a new game.The thing is, you will not be seeing all of the new content if you load a save from 0.06.
Most new content requires variables to trigger that weren't in 0.06 and also a big chunk of this update is lower stage content for Lisa, Amber, Marie and Cayenne.
Did all of the earlier events trigger? Yeah can't answer that. Was it a bit glitchy and some what odd.. yeah.