I feel bad for him but it still comes across as not taking full responsibility for (or even fully understanding) the mistakes made.
I totally agree. There were brief mentions of the improper mooring ball at 21:40 but zero responsibility accepted. And I'd have to believe that his willingness to not sue or litigate is based on legal advice that he was negligent and it'd be hard to argue and win a case to get the claim accepted.
Hmm, I thought he DID take responsibility for mooring on the ball in bad weather. And, more interestingly, the expert he had on questioned the difference between a navigational error (hitting a reef) and this mooring error and why this was seemingly different. The expert talked at length about how this policy looked a lot different than others he's seen as well as how strange the communications and behavior of the company was throughout the whole process. He, the expert, did say that he looked at Hillbilly's "No Steering, No Problem" video and felt he was going to have a tough time but then he also said that this particular incident was not due to the steering issue (basically, he was not steering at the time so it shouldn't matter). The expert pointed out that the "seaworthiness" criteria can be used maliciously, using the example of a claim denied for fire extinguishers being out of date for an incident that wasn't about fire.
Hillbilly also said part of the reason for not pursuing legal action was because the jurisdiction would have been in Costa Rica (which was also very odd according to the expert) and would have required even more expense and he'd be playing in "their home field".
The whole thing gave off a vibe of this insurance company being somewhat scammy. Now maybe that's the vibe the Hillbilly wants to have come across to try and absolve him of liability but it seemed like the expert agreed to some extent.