When splitting the party becomes the default, normal path for the players in a group, what does that tell you? Well, if you want your players to stay alive, and your campaign to continue, you need to adapt your villains to keep in touch with what your players are doing.

Han does not seem to take this with proper seriousness. I'm wondering if he's lost some brain cells with all the identify shifting he's done.

As much as Han is supposed to be Chewie's Sidekick, he seems to be taking charge. That's not normal. A sidekick basically being in charge sounds like... well, actually, when have we seen a sidekick in this story? The only one I can think of was in Butch Cassian and the Sundance Droid, where Pete's characters had one set of senses over two bodies. The secondary character was a sidekick, but he never took charge. Although, one set of senses, and controlling two bodies, that sounds like Sally during the droid factory. But again, we never saw anything happen there either.

Maybe looking at teacher/student relationships? Well, in that case, Episode II had a very active student who ignored his teacher or just plain took charge and did things (thinking of the car chase near the beginning, chasing down the shapeshifter) without actually going against his teacher's non-existent instructions. Or, Episode V, where the student was basically told "don't go", and went anyways.

So, this is sort-of a call-out to campaigns II and V, which is just right for this campaign if they are following the Ring Cycle stuff. Except that this would require Han to be Chewie's student.

Chewbacca a teacher to Han? I just don't see Jim being a student in-game. After all, he's a student in life, and uses these games to turn off his brain. And a student that just doesn't pay attention and turns off their brain? That's not realistic, is it? :-)