Hey there, so this is my first post here ever, but I thought I should share my experience with you. I have been GMing all sorts of systems, settings and campaigns for over 25 years now an when a friend of mine asked me last year, if I would like to start a new pen&paper-group with him and a bunch of other newbies, I thought "hey, what a cool chance to show this awesome hobby to a new generation of players!"
After deciding to settle on Pathfinder, since I already had a ton of books, I choose the Serpent's Skull AP, as I've always had a special love for snake-themed villains in fantasy. We started out with Smuggler's Shiv last February and it was awesome. After about roughly 40 hours, we finished it in late August. In September we started "Racing to Ruin" and so far it has been one wild ride, since my players really tend to screw things up due to unwise decisions, hesitation in timecritical moments, bad dice rolls and deliberately not acting as a team since they left Smuggler's Shiv. For me as a GM this means a lot of work, but also a lot of fun watching them fail (which is very strange, since I'm usually very Pro-player as a GM).
It all started, when they managed to get Gellick, Aerys and Jask killed by the cannibals on SS. To make things worse, the party showed open dislike for the other two survivors (Tasha and Ichiro) even before that. They even murdered the Tengu in cold blood. After they had arrived in Eleder and the factions contacted them, things escalated even more. Within a couple of hours after meeting the factions, the party got in a huge argument which faction they should join. Two were with the pirates, one was with the Pathfinders, one was with Aspis and one was with Mantis (out of fear). They somehow managed to arrange themselves with trying to get the pirates and the Pathfinders work together (and right after that the party's druid seduced Amivor). They even managed to have succeed on their diplomacy checks and thus a new alliance was formed. Everything worked out fine...or so I thought. Suddenly I get a private note from one of my players stating, that he wants to make a deal with Aspis, to work as a spy for them. So I met with that player separately and we roleplayed an actual pretty cool negotiation scene between him and Dargan Etters.
Two days later, the slave insurgence took place and despite telling my players straight to the face, that immediate action is crucial since they kidnapped Amivor (since neither Aerys, nor Gellick were still alive at his point and the party's druid actually was starting to become sort of a romantic interest of Amivor), my players hesitated to storm the Whaling Company. I told them things could get out of hand very fast and in order to save Amivor, they should act quickly. Instead my players decided to take a stroll across town, to hire a fisherman to row them to the Whaling Company from the seaside. No fisherman was willing to get into the fray, so they went a different route and tried to get the city guard to solve the problem. I told them there is a huge smoke pillar coming from the Whaling Company, which had the effect of them wanting to avoid storming in there even more. The whole scene took us more than 5 real world hours to play through, which roughly translated to 7 hours in game time, by which I decided "ok, they might be new to this game, but not being heroes must have consequences after all". Hence Amivor got killed. My players were devastated. We finished the session and I talked to them, about the whole situation. They seemed to understand, it was their fault.
Next session they dealt with the Pathfinders pulling out of the alliance, so now they are stuck with the pirates. They were not interested in dealing with Nkechi, since they had a jungle druid who thought she could handle everything Nkechi would otherwise do for them.
The expedition eventually started and at first it all went well. They absolutely proved themselves on the route to Kalabuto. Then came the assassins ambush in Kalabuto. They stroke at night, when they were asleep at the inn (they explicitely did not want to stay at the dwarf's house). Two of them made it very clear, that they would like a single bedroom, since they don't wnat to deal with the rest of the party's snorring. Long story short, one of them did not survive the night. To make things worse, they decided, that traveling by boat up the river is way more comfortable, than walking through the jungle. I told them over and over again, that their job is trailblazing for the expedition, but I guess I already had lost them at this point, since they looked me in the eye, stating "screw them, we gonna go to Tazion on our own and claim all the fame and all the loot for ourselves". Then it hit me: "Congratulations! You have spawned a new generation of murder hobos!"
To be honest, I was a little disappointed at first. But then I thought to myself, I might as well roll with it and watch them realize, that they eventually will need the help and support of one of the other factions and I'm really looking forward to that day.
Apart from that, I really love this AP and its whole theme.