Freeport on the Corsair Coast?

While I actually already came up with a pretty drafty Corsair Coast 5x5, the reality is that it's at least as much a Timischburg coast 5x5 as it is a Corsair Coast 5x5 (just like Cult of Undeath ended up becoming as much a western Hill Country 5x5 as a Timischburg 5x5), so there's absolutely room for more Corsair Coast action. Of course, I'm wondering, with all of the Freeport material that I'm about to dive in to, if there's an opportunity to adapt it into a 5x5? I already know that there's lots of silliness inherent in Freeport; it's way too fond of pop culture references, puns, and poor dad jokes when it really kind of wants (I think) to be taken seriously like a pirate-horror take on fantasy. However, even if I take all of that out, there's so much adventure material that I think that I can still come up with more than enough material to make it work. I've got a whole Pathfinder style adventure path, fer cryin' out loud (Return to Freeport) that I haven't even read yet. Plenty of the original trilogy can be reworked to my taste without too much trouble, as I remember it anyway, and there's even some stuff in Black Sails that is salvageable. Although less than you'd like, unfortunately. That was the low water mark for silliness in Freeport.

If, for some reason, I can't seem to find enough good material in the Freeport stuff per se, I've also got the related Bleeding Edge adventure series. The final module in this series is "Dark Wings Over Freeport" but all of the previous volumes take place in the Freeport campaign setting, albeit not in Freeport itself.

Sadly, what will not be very useful, I don't think, is the Pathfinder piratey stuff. I don't remember being very impressed with the Skull & Shackles adventure path for even the whole piratey nation concept from Golarion. Real disappointment. 

Still, it also motivates me to dig through my boxes and find my copy of Captain Blood again. It's been many years since I've read that or Scaramouche, and I dearly love both novels. 

So, relative to Freeport, how do I want my own Porto Liure and Corsair Coast to differ? Let's make a small list.

• Freeport is way too overtly D&Dish. I've commented before on this, when comparing Freeport to Five Fingers. While Freeport is supposedly systemless and settingless (mostly) meant to be plugged in to any setting you need, the reality is that it's obviously meant to be plugged into a D&D setting, and it makes all kinds of basic assumptions about the fantasy setting that are only compatible with D&D or D&D-like games (like Castles & Crusades or Pathfinder.) Five Fingers, on the other hand, while explicitly part of the Iron Kingdoms setting, feels in some ways easier to adapt to a darker, lower fantasy than D&D. I'm not sure how I'd go about specifically making these changes (yet) but that's part of the reason I want to at least skim the FATE and Savage Worlds companions; I kinda want to see what they do.
• The Golden Age of Piracy, which Freeport is overtly imitating, is not completely compatible with the Medieval period that D&D is more (usually) overtly imitating, from a social and technological standpoint. Then again, D&D (and Shadows of Old Night even moreso) borrows some social conventions from the Old West, Colonial America and the Colonial holdings of the pirate era that are kind of appropriate. But don't expect cannons, broadsides, and tall ships, etc. (in spite of the picture above) very much; Medieval style cogs, caravels and carracks, not much more advanced than what Christopher Columbus used to sail the ocean blue at the most advanced. Although I do officially have an option in my appendices for black powder weapons, I'm more interested in swordfighting and stuff like that than pirate gunfights too. This is kind of a line Freeport itself tries to straddle; stuff looks like the Golden Age of piracy, but doesn't actually act like the Golden Age of piracy with ship to ship battles in the traditional Golden Age of Piracy style.
• Freeport is too silly. There's a ton of puns, magical mishaps, and other stuff that just doesn't fit the darker tone of Shadows of Old Night. I don't mind some dark comedy at times, but it needs to be played against a straighter backdrop. This is why I keep comparing Freeport to Five Fingers all the time; Freeport is a good setting, but Five Fingers actually has the tone that I wish Freeport had. Freeport is familiar with that tone, but then can't help dipping into in-jokes, pop culture and puns.
• Freeport is (probably) way too woke. Green Ronin have gone all in on wokeness, and I can't imagine that the more modern stuff isn't woke; you can tell just from the cover art with the diverse grrlbosses all over the place, and the fact that they got confused ladyboy Crystal Frasier to write some of their stuff. I'm absolutely wary about stuff that will have to be cut for this reason. Even some of the earlier stuff was borderline; orcs as obvious metaphor for black people in the ghetto, etc.
• Freeport is a tiny little island, whereas my Porto Liure will... well, I guess I need to decide. I'll probably put Porto Liure, my analog to the city itself, on an island too, but it'll be within sight of the mainland. Kinda like Cozumel, but flipped 180°. The ocean is to the west in Shadows of Old Night, so Gandesa Island (I'll probably re-use) will be a small group of islands just to the west; a mile or so at the most, from the mainland.
• I like the idea of the snakemen backstory, based in some part on Howard/Lovecraft stuff, but snakemen as sympathetic people who just happen to have snake heads doesn't work for me at all. They're all monsters. I already know that the K'Stallo stuff from the original trilogy will have to be modified, and that's not even getting into the modules that follow. I might replace Yig with something more like Sertrous from Elder Evils, although it needs a new name. Zo-Kalar, an obscure Lovecraftian name who is also corresponding to Zargon in some of my work, might be a good one. It changes the tone too to get rid of the obviousy and overt Lovecraftian stuff; a more obscure (or even new, unique) name that fits the Yog-Sothothery vibe works better than a really familiar one.
• In fact, in general, as much as I like adding Lovecraftian Yog-Sothothery to my fantasy games and settings, it can go very wrong if it's too familiar and comes across as a wink and nod in-joke or reference without actually managing to hit the proper tone and themes. This is, again, one of Freeport's significant failings, I think. Not only are the serpent people just ripped flat out from "The Mound" and "The Shadow Kingdom", but then they're made sympathetic and turned into the good guys of the story. Or at least, one of them is.