Logistically difficult. Everything that led to the differences between the two Enzos would have to have gone in such a way as to produce my version rather than Matrix: he wouldn't have lost that one Game and ended up Game-hopping for years. It's even debatable whether my Enzo could have been produced by the course of events including Megabyte taking over and Bob being lost in the Web. Something close to my version might have happened if they had simply closed the Web portal without Megabyte's double-cross—he'd be a cadet due to the Web war, but he wouldn't have been thrown into active duty so suddenly and could go to the Academy for training—but there would still be differences. AndrAIa would be his girlfriend, unless she never left her Game (see AndrAIa's What-If), and there wouldn't be the age offset due to his copying. And, of course, canon after season 2 would be completely different, in ways that can't really be extrapolated past "life goes back to normal, such as it is."

Not so much a "what would happen" as a "what would have to have happened to lead to that in the first place?"