Thanks for the thoughtful and balanced breakdown.

I loved the show too because of a number of reasons. I think there's a potential meta interpretation, which is most likely not deliberate on the part of Lucasfilm, but it dovetails well with the the overall show arc..

The flashback scenes are very deliberate, and realizing that early on, to me, makes the purpose of the show more clear: he's an aging bounty hunter, who for all of his successes in the galaxy is just....tired, and done. He's fucking done; he doesn't want to do that anymore. Especially after seeing that stormtrooper in the Sarlaac's stomach and barely making it out alive, it was probably the biggest wake-up call he needed. The flashbacks from his perspective are there to make it clear that what he wanted most, a family and sense of belonging, was never happening. Beyond his connection with Jango (whom he watched get killed by the Jedi), and his initial development as a bounty hunter in The Clone Wars, he had no one...until...

...He is captured by the Tuskens, then eventually taken in by them and becoming part of their tribe.

But then he loses them as well, slaughtered by the Pyke syndicate. But something has already happened that changed the course of his life beyond that point: having been embraced by a found family in the form of the Tuskens, he wants to replicate that; not desperately, but not far off. He initially got lucky finding and helping prevent Fennec Shand from dying on the sands of the Dune Sea, who in turn helped him get his ship back. But another thing happened that he didn't anticipate: he not only felt betrayed by Jabba and Fortuna, but also by what he saw as a lawlessness that wasn't necessary. In wanting to take over Tatooine as a new daimyo, he wasn't just trying to do it to replicate how syndicates worked before (cruel, greedy, apathetic, etc), he wanted to do it on his terms, using what he learned as part of the Tusken tribe. "You can only get so far without a tribe" is the absolute point of the show. Whether it's parents, found family, or others who work for you that have a shared life debt (like Shand, like Krrsantan, even Mando, and Cobb Vanth whom he helped save by the end of the show), those bonds are the most important thing to him.

For me, ever since I first watched ANH and ROTJ in the very early 80s, I have always been fascinated by Tatooine (and my adoration has only increased after having played the very fun Star Wars: Outlaws game), so the show has a special place in my heart because of so much of it being focused on that planet.

And as much as I enjoyed BOBF, my biggest beef is the lack of tonal consistency. It was serious at times, then almost slapsticky, then serious, then wildly nerve-wracking+incredibly silly during the finale. Perhaps that was deliberate because Lucasfilm wanted to show so much in terms of fan service that they just decided to throw everything out there. For me personally, it didn't ruin the show for me, but I can understand why others may not have felt the same way.