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I've been thinking about this a lot in prep for my own campaign.

Lintekarka hits on a big part of it. Not much piracy happens in the Shackles. Instead, the pirate raid north of the Eye, and use the Eye itself to cloak their approach and guard their retreat. As part of the initiation into the Free Captains, the Master of Gales teaches them the secrets of the winds and waves, so they can sail deeper into the Eye than other ships.

There are also trade routes within the Shackles. You can't have cities that large without a way to move goods around. Each Pirate Lord is master of their own fleet, ostensibly made up of other pirate ships, but as a practical matter, many of them are simple merchant vessels paying a protection fee to one Pirate Lord or another for the right to fly under their flag. How safe this actually makes you depends on the shifting politics of the Pirate Lords. There are some pirates who refuse affiliation with any of the lords, raid ships as they see fit, and operate independent harbors far from the influence of Port Peril. I've made Firegrass Island one of these harbors in my campaign, and made all the hostile pirates they encounter in book 2 independent pirates operating from here.

Saragavan trade ships can usually pass freely through the region, thanks to the Saragavan Deal, but there's a schism among the Free Captains over the slavery issue, and some Pirate Lords argue that the Deal shouldn't cover slave ships. Some, like Jolly Raffles, openly attack slavers, and dare the other pirate lords to do something about it.

While politics prevent Saragava and Cheliax from officially trading with each other, Cheliax's imperial ambitions require vast amounts of slave labor, and Saragava is desperate for markets for its slaves, since it relies on the slave trade to break up local communities and make it harder for them to resist their colonial control. The Rampore Islands, under the control of the rakshasa Bedu Hanji, has become the middle man in the Saragava-Cheliax slave trade.

What would happen in the region (in both timelines - original and 2E) if the players just sold off the findings from book 1 and went off on other adventures

Since my base plan is to do this rather than the whole AP I haven’t checked out the metaplot. Is there a background rise of serpentfolk that will not be put into check by the presence of adventurers

I guess I am just wondering if there would be any consequences (in theory) to just selling what is uncovered on the Shiv to the highest bidder

The Big Evil Plot in Serpent Skull is an attempt to resurrect the slain deity of the Serpentfolk, Ydersius. Led by a living god, the resurgent serpentfolk empire would be a massive threat to the world. There are ancient vaults scattered across Golarion, filled with serpentfolk in suspended animation, waiting for the return of their god to awaken and continue their war against the Warmbloods. At the very least, Mwangi becomes the seat of the new Serpentfolk Empire, which immediately begins expanding into neighboring countries. Worst case, armies of serpentfolk boil up out of the Darklands all across the planet, besieging every major nation.

Of course, as a GM, you can avoid all that by just deciding that the group the party sold their notes to was also a bunch of adventurers, and they went off and stopped the snake apocalypse while your party was doing other things.

About halfway through book two, I had this idea I really dug about how to run the AP with characters who were genuine heroic types, and not villainous henchmen, before they lost their memories. By that point in my game, I'd already solidly established that my PCs were monsters* before they became amnesiac, so I couldn't use it myself, but I wanted to share it, particularly because I've seen some GMs hesitate at making their players run (formerly) evil characters.

The lore on Xhamen-Dor stipulates that he doesn't really have organized cults, with one exception - the Sentinels, a group that "worships" Xhmanen-Dor with the goal of preventing him from waking up. They're dedicated to wiping out any evidence of his existence, and to prevent being corrupted through their knowledge of the Great Old One, must periodically wipe their memories.

You see where I'm going with this, right?

Before they lost their memories, the PCs were members of a Sentinel cult. They still have an unsavory reputation, because they often had to kill some apparent "innocent" who had been seeded by XD, and of course, they could never defend their actions, because explaining why they killed the seeded exposes anyone hearing the explanation to Xhamen-Dor's corruption. Lowls was still their leader, but instead of betraying them in a power grab, he was saving them from being taken over by Xhamen-Dor, but was tragically unable to prevent his own corruption in time, and now his former companions have to hunt him down before he awakens the very creature he had dedicated his life to keeping asleep.

This change requires virtually no change in the actual campaign - pretty much everything plays out exactly as written, including everyone in Thrushmoor acting like the party is evil, but PCs can still have been genuine good guys all along. (Well, no major changes through book 3, which we just finished, and I don't think this breaks anything in the next three books, but I haven't actually run them yet.)

*in one case, literally - the party wizard was a Leng ghoul, polymorphed to pass as human before she had her memory wiped.

Though I sorta wish I had yoinked the pictures to use as props for Zandalus...

I was googling imagery I could use for inspiration/handouts for my players, and found this artist, Michael Hutter, who did a whole series of paintings based on Carcosa. I picked sixteen that I really liked, and printed them out. Then I googled "magic circle" and found some sufficiently arcane looking design, chopped it into sixteen sections, and printed one on the back of each of the paintings I'd printed out, then scattered them throughout Briarstone. Once the players had collected all sixteen, they had to reassemble the circle on the back to get a minor magic text as a reward.

I did something a little similar - I did pre-generated characters that my players selected blind, without knowing anything about them. One of them was a Leng Ghoul who had been polymorphed to look human before they had their minds wiped. She didn't figure out what she actually was until about halfway through book 2.

My take on Lowls not just killing the PCs is that he actually liked them. Lowls is more than a bit of a loser, and having an adventuring party was a big deal to him. That's why the Mad Poet demanded that particular sacrifice - Lowls had to give up something important to him to get the information he wanted. After the sacrifice, he spared them as basically his last act of human compassion before the Xhamen-dor corruption overtook him completely.

Obviously, I had to modify the backstory a bit to remove the part where the party were Lowls' slaves.

Am I too overprepared if I created an entire table of random dreams based on different themes within the adventure path? In total, I have 36 dreams including some that are Hastur related (Tatterman is a minion of Hastur), Xhamen-Dor related (PCs are infected through Lowls), Carcosa (empty city that Zandalus dreamed), Briarstone related (I think there's some cool background the PCs can't really learn as written), Dreamlands related, and plot related.

I made my players a deck of illustrated dream cards that they randomly drew from every time they slept.

So, I'd say underprepared. :D

My party finally went to Iris Hill, after I sent them a literal invitation - Melisenn asked them to come over for lunch. They were pretty certain that she was the main villain of the book, but mostly because they're pretty genre-savvy players, not because of anything concrete that had turned up in the game, so they immediately expected a trap. This led to two of my favorite bits of player dialogue I've had recently:

Player 1: This is obviously a trap.
Player 2: Yes. We should bring snacks.
Player 1: What?
Player 2: If it's a trap, there's not going to be any lunch, is there?

and

Player A: I think we should go, not through the front door. Let's sneak in through the back!
Player B: And then what? Fight our way to lunch?

Anyway, lunch went off without a hitch, and now the players are convinced Melisenn is innocent and a potential ally.

Mwahahahahaha!

Is it revealed anywhere where Count Lowls got his copy of The Chain of Nights?

I don't think it's explicitly described as the same copy, but its mentioned that the event that drove Zandalous mad occurred when he was on an expedition with Dr. Henri Meirtmane to recover a copy of The Chain of Nights and was kidnapped by the cultists who owned it. I think it's mentioned in Thrushmoor Terror that Lowls' second published book was a take-down of Meirtmane's scholarship, so there's a bunch of history there you could tap to elaborate on the backstory.

My group has just gotten through Hailcourse - like many others, they decided to scale the walls, and inadvertently pulled nearly the entire fort. They won, and now know that somehow the fort was overrun by Deep Ones. (I replaced the Skum, because why not?) I had some half-formed ideas about how to do the rest of the book, and they all just sort of snapped together in my head when the party finished the fort, and I wanna talk about it.

I stole an idea someone else put forward in this thread, about there being multiple factions of cultists. There's Melisenn and the Hastur cultists, Daridela, Ariadne, and Queveandra (from book 2) are all hags, and part of a coven dedicated to Xhamen-Dor. And the Deep Ones are, naturally, Dagon worshipers.

Melisenn cut a deal with Lysie Brilt (from the smokehouse) to help finance her plots (the Lowls estate being basically bankrupt) with treasure dredged from the lake bottom, in exchange for basically giving over the town to them. She's been systematically removing the leadership of Thrushmoor, and helped open the gates to the Deep One take over of the fort. He deal with the lake-dwellers is for the town, which the Deep Ones are planning on invading, plundering for breeding slaves, and slaughtering everyone else. It's a double-cross, though: Melisenn wants to use the invasion as an excuse to get as many citizens sheltering in Iris Hill as possible, so she and her cultists can sacrifice them in mass, triggering an incursion by Carcosa. Anyone in the town when this happen is twisted into servants of Hastur - byakhees, and the like - and that includes the Deep Ones who will be swarming the town.

The hag coven has been helping the Hastur cultists, but mostly out of a sort of professional courtesy. They've been playing a longer game, subtly grooming Haserton Lowls to convince him to become the vessel of Xhamen-Dor. They don't care if the plot to take Thrushmoor works or not - they plan to hand over all of Golarion to Hastur by having it become infected by Xhamen-Dor.

The party hasn't tried to go to Iris Hill yet. When they do, Melisenn's going to let them in, and be as helpful as she can in uncovering whatever dastardly thing Lowls might be up to. She presents herself as an old college friend of Lowls who stepped in to help him out when he got into financial trouble, and is terribly, terribly concerned that he might have gotten into something dangerous. I'm hoping this throws them off for a bit, and encourage them to do more snooping around town to follow up on some of the side-quests I've planted. Eventually, this will lead them to Daridela, whom they haven't encountered yet. (I skipped over her as the first set piece in the book, because I knew from the outset that I wanted to do something different with her.)

Daridela will spill Melisenn's whole scheme to them, because the night they find her is also the night Melisenn's scheme comes to fruition, and Daridela doens't really care if they can stop it or not. They race back to Thrushmoor, and have the choice of either helping to stave off the Deep One invasion, or heading directly to Iris Hill to prevent the ritual from being completed. I'm trying to work in an angle where they can go to the Deep Ones and somehow demonstrate that Melisenn's stabbing them in the back, which leads to the fish people attacking Iris Hill themselves, resulting (I hope) in a three-way brawl between the Deep Ones, the Hastur cultists, and the party.

The only thing I haven't figured out is how to get the party introduced to Lysie Brilt - they don't have much reason to go to the smokehouse on their own - and then get them to try to dialogue with her when she and her fish cousins invade the town, instead of just making with the stabby-stabby.

I've made a few other changes I like: the revenant isn't some guy that one of the PCs accidentally beat to death - instead, he's the guy one of the other PCs framed for the murder of some guy a PC accidentally beat to death. He's now the owner of the bookstore that Lowls drove out of business. Lowls had the PCs frame him so he wouldn't have to pay his debts. The party learns about this from a combination of recovered memory fragments and documents they found at Hailcourse.

Also, I felt that between the ghost in the basement of Hailcourse, and Nemira Lowls' "ghost" walking the streets of Thrushmoor, putting another spirit in Wailing House was a bit too much. So, there's nothing in there. There's still an unearthly screaming coming from the house every sunset, but if the PCs investigate, instead of a wraith, they find a series of tunnels connected to the lake that the previous owner had used for smuggling. A quirk of the shape of the tunnels creates a vacuum when the tide goes out, and the "screaming" is the air rushing in to fill the vacuum. Normally, a trapdoor sealed the tunnels off and prevents this effect, but the last owner of the house was killed by his smuggler associates, and they left the trapdoor open.

Here's a pdf of the cards I made for Serpent Skull, with the art blanked out. It's about 80mb.

There's three basic card types: artifacts, installations, and creatures. Artifacts are anything that can be picked up and carried away. Installations are buildings and statues and things that are generally not portable. I didn't introduce the creature cards until they got to Ilmurea, where the products of Serpentfolk fleshwarping laboratories had escaped their cages when the city fell, and then spent 10,000 years inbreeding while being exposed to weird science radiation. There was a LOT of weird stuff scurrying around down there!

The pdf was formatted for ease of printing, not ease of reading. Sorry for all the upside down cards!

Initially, I was using Ultimate Campaign rules for the player's camp, but ended up dropping it because only one of my players was into it, and everyone sitting around while one player did all the camp stuff was no good. Some of the earlier cards reference those rules, but they stop showing up after a while.

My friends will confirm that I have a long history of screwing up Google Docs links, so let me know if there's a problem with viewing the pdf!

I'm not there in the campaign yet, but my plan is that making the Knowledge check to recognize the painting allows the PC to recognize that it represents a being known as the Inmost Blot, but not its actual name - because there's almost no book anywhere on Golarion where that's recorded. Later, in Lowls journal, they'll find an entry where he talks about learning about Xhamen-Dor, except in the entry, the name has been scribbled out. In a subsequent entry a few weeks later, he explains that his research has uncovered the infection side-effect of the beings name, and he went back and covered it up in his journal so it won't affect him. He muses that his "intense mental training as a scholar" gave him the mental fortitude to protect himself from exposure. The next two pages are stuck together, and when the PC pries them apart, it's just "Xhamen-Dor" written over and over again.

That's incredible! Are you able to share your discovery cards? I would love to see them!

The art is just stuff I grabbed using Google searches, so I'm a little concerned about sharing them because of copyright issues. I might put up a few of them with the art blurred out, though.

Consider adding fabled treasures to the city. I put one in each district and tried to make them things that tied into the ancient history of the city. I just made it so that Urschlar hid many of them, in addition to the argental font. I generally just put them in a five room dungeon, that could be done in a session. Some examples were a drum that disrupted serpent folk telepathy and mental attacks; part of the regalia of the ancient kings and queens that helped protect against aberrations.

...

Depending on your players you can use the discovery point system as well. As presented it is pretty abstract, but I made little partial clues for each discovery point that could slowly be pieced together in order to get a picture of what had happened to the city. I also included clues about the fabled treasures here and and clues that could help bypass some of the traps and puzzles in the fabled treasure dungeons.

I did something pretty similar. I didn't really like the way Book 4 was integrated into the AP, so I changed a few things. First, the vaults were available to be explored from day 1. Second, the stones needed to get into Ilmurea were not hidden 1-to-1 in each vault. I scattered them about the city more. I didn't want them to be obvious, "This is a key, go find a door," objects, so I made them into Ioun stones, tied them to the seven Azlanti virtues, and wrote a short bit of doggerel that described the Azlanti view of the hierarchy of virtues. Essentially, telling them the order the stones needed to be placed in order to open the portal.

And here's the part where it was fortunate that I was working on this part of the AP during a period where I was unemployed for about two years: I made a deck of "discovery cards." Basically, I used Photoshop to make a card for every bit of loot in Saventh-Yhe that had any description to, and a card for every building in the city that was remotely important. And then I invented a bunch more. By the end of the AP, I had a deck of almost 300 cards. Mixed in were the seven Ioun stones they needed to unlock the door, and fragments of the poem scattered across various murals, carvings over door lintels, and engraved on various other random objects they found. They spent easily half a year, real time, exploring the city and gathering these cards before they figured out (from other clues I hid in the cards) that there was a second city underground they had to find, and a portal to get into it.

The session where they spent almost two hours, going through this massive stack of home-made cards, looking for clues and arguing over the order, without me having to give a single hint or nudge to get them in the right direction, was the single best experience I've ever had as a GM.