I did a playthrough with the 2.2-2.3 versions, and my problem was that as the end of 1998 approached, I was woefully unprepared. Having fewer progress-critical missions, and not savescumming if I fail to capture the target alive, really hurts. Also, as I have to play hundreds of standard missions, even playing very carefully, occasional mistakes (or extremely bad RNG) do happen, leading to a lot of attrition, slowing my progress even further.
And I prefer to dive into the game (and new updates) blind, without too many spoilers about what I should be focusing on or preparing for.