The flashback scene overlaps Michael sitting in the same room where he basically told Connie to get rid of Earl. The last scene of II is Michael sitting outside on the grounds of the compound; he's not smoking (and he is still wearing his wedding ring).

I doubt that we can accurately gauge the year. Some Board members who know the cars of the era may be able to identify the approximate year based on the cars that appear in those scenes. In the hotel scene when Michael strikes Kay, both kids are young, nowhere near college age. The same is true in the scene when Michael closes the door on Kay.