Well, we're officially done with Sigil. Not sure if I portrayed the city right or wrong but by the end they were willing to let the city tear itself to shreds, but luckily there was gold involved to motivate them to do otherwise.
The main story, as I described with the key to tradegate missing, was worth 18,000gp for them to merely locate the key and figure out what happened. They were at least sympathetic to the fact that the courier (whom they hired lothar the old to cast a speak-with-dead ritual) wanted his mistress and lovechild to remain safe (and wealthy) and decided to concoct a made up story for Estavan as to why the recipient of the key ultimately ended up with the key. They never thought to investigate further with the mistress and figure out that the original plan was to raise dead, I decided to leave that lie.
They fumbled around enough during the quest for the key that I described them stumbling into the scene of riots after a failed streetwise check. Rather than try to navigate around, the wizard decided to use his might to quell the riot. When this went catawampas, I felt this was an appropriate time to give them a hint of what the Lady of Pain's presence is like. I described them feeling an overwhelming sense of dread, and how small bleeding cuts appeared all over their bodies as they got closer. Ultimately they were incapable of getting a direct glimpse of her, but they saw that people in the riot had been randomly flayed.
Anyways, I had created two methods for exiting the city, and while briefly flirting with the idea of finding the key and leaving with it, thus preventing the city from getting enough supplies in time for the festival of doors, they ultimately decide to sign on with a captain of an astral ship to take a roundabout way back to the prime material plane.
In retrospect I understand why people advocate aligning PCs with certain factions, as it gives them a sympathetic ear in the city. It didn't quite work out story wise, but as other have pointed out to me, there's a reason Sigil isn't called "The city of brotherly love". I think if I were to do it again, I would try to find more ways to impress upon them that the city is full of extremely powerful beings, not just the lady, and that crossing them is a mistake, rather than leave these powerful beings as window dressing.
All in all, pleased with the results. Next: an adventure in the astral sea, aka pirates of the caribbean in space!
And nice handouts btw, very thorough.
