I mean, not to get too deep into black sails discourse, but I don’t think the show ever presents what happened at the end as a good thing. But considering the historical realities and what happens in treasure island, it was basically how it had to end.
I mean the only successful slave rebellion in the Caribbean was the Haitian revolution a whole century later. As much as I would have loved to see them wreck the british empire, the show does tend to stick pretty closely to actual history. And pirates do end up being pretty much wiped out in a couple of decades. That sense of inevitability, that this is the end of an age, is actually one of my favourite things about the show. But yeah, they definitely could have given more screen time to the maroons (petition to replace every rogers sex scene with more julius please), but that’s really the only fault I find with show? I think in general the show does show pretty well that their anger is completely justified and never condemns their violence.
spoiler
And Flint gets Thomas back, sure. But I doubt he’s ever completely happy basically locked up in a plantation forever. The whole “ disappear and never be seen again” is literally what the admiral guy threatens to do to him, so I don’t think it’s ever portrayed as a good thing. Plus Madi’s gonna be absolutely miserable and John Silver loses everything. Not necessarily a fairy tale ending for any of them!