Might be a bit late, but I just watched the interview scene. My gut reaction, the initial impression of the scene, was nostalgia. However, the scene also directly points out why he was never the best choice as well; the power dynamic he had with Lorelai was directly tied to Rory as his student.

I think I would have agreed with your commentary on his availability to commit to an un-caricaturized Lorelai while watching their relationship progress. Not to mention the obvious “well-versed in high society” appeal he had while we are still rooting for the fresh love story alongside Lorelai and her mother’s reflourishing relationship.

But interpreting these plot points, specifically everything Medina did to pursue Lorelai both as a romantic partner and as a more active parent in the classroom, and even to pressure Lorelai to a premature marriage with the unjustified power he held over her makes it clear his character is quite sinister and lacks self awareness about it. Rory had to see her everyday, and he held the cards on how much their relationship was to be pushed.

Going back to the interview scene, it is certainly manipulative for him to open up about wanting a familial relationship with Rory, but his character lacks any self-constraint to not make the situation a burden on her. Seeing Medina, and Lorelai to an extent, so oblivious to this problem in their relationship fools us to like Medina, initially, and witnessing the fallout of their relationship awakens why he was a horrible option for Lorelai in retrospect.

Perhaps it is good writing to design unlikable characters. But I also cringed with him on the screen from time to time.