I don’t think Pac was “naive” he was idealistic in the sense that he really believed in the teachings of Black Panther knowledge and brotherhood and his lineage of having Afeni as his mother would enable him to transcend “streetcodes” and I believe he actually had some level of success doing that in the Thug Life era connecting with different gangs from all over.
He then realized with the Henchman/Jack drama that some dudes don’t honor or care about whatever lineage Pac came from and he admitted that mistake in his phonecall with Monster Kody later on.
After that it seems like Pac went from an idealist to a Machiavellian which is an 180 degree change in terms of the worldview and became more jaded and nihilistic. He vowed to get his money up and get his revenge but got caught slippin in Vegas and met his demise. Maybe he was trying to balance the idealistic and Machiavellian sides better because towards the end of his life he was preparing the One Nation project which in and of itself a project based on an idealistic premise but probably be funded and promoted by the money he got from his Machiavellian ways.
I don’t believe Pac became affiliated with the bloods because it was some cool shyt to do. He thought it was a means to an end, a tool for a larger end goal but it was an incredibly fine line to walk on and as a young dude with temper, he made the wrong decision to personally step up to Orlando that fateful night.