I think like everything in the show it’s nuanced. He’s supposed to be a completely oblivious aging white male celebrity. He can never fail in a way that ends or damages his career. Cheating on pickles means he lucks into being the face of depression, his bankrupting spaghetti strainers save the day. He’s not completely untalented (Diane compliments him for Philbert) or malicious (forgives bojack on his show, nominates bojack for Oscar) but I don’t think that means he’s hiding some deep intelligence. He also acts selfishly (Cordova/Hank saga) and feeds into his own delusion (angry with Diane about questioning relationship with his brother, denial about dead mom and dad).

The show portrays a lot of different ways of dealing with relationships and weighs pros and cons of each. PB struggles with personal relationships and maturing but his happy go lucky “can-do” and forgiving attitude has value in situations with Diane and Bojack who so often feed into depression and pessimism. It’s important that someone can forgive Bojack (offers to house him post prison) and Diane (hiding out with Bojack) unconditionally, even if we see how that can negatively effect PB in the long run.

Diane and PB’s phone conversation in season 6 encapsulates this all really well. Sorry for long form analysis I have autism and an English degree.

Lot of play references in Bojack!! I immediately think of “How I Learned to Drive” by Paula Vogel with the Penny’s story. I think the report (Max?) asks Penny where she learned to drive in the last season.