So we just ran things last night, and I think it went pretty well.
My group had already gotten the real Trinia out of the city when they first caught her, so when they heard rumors that Trinia had been caught, they met up with Vencarlo (who had worked with them with Trinia before). Vencarlo told them he was trying to get more information (from his friends whom Trinia is living with, or seeing the new captured Trinia in the castle), but not having luck with either.
They spent the next couple days before the execution planning (scooping out the location, attempting to do small acts of sabotage to the stage, etc). Vencarlo told them he was in touch with other people, and suggested they place themselves in a particular part of the square, where a storm drain grate was loose, allowing for quick/hidden escape out of the square, and to keep themselves open to help should something come up.
During the execution, events proceeded as scripted--Blackjack interrupts, chaos erupts. My team aided--one tried to Message "Trinia" but got no response, another had their familiar set off a thunderstone in the middle of things to cause more panic and confusion to aid Blackjacks rescue. They then Messaged Blackjack that they were allies and had an escape route. With some Darkness behind to cover their escape (and to continue to cause confusion, they dipped into the tunnel, out the other side, and then through the Shingles to get to a safe spot.
I ran the tunnels/shingles as a group skill challenge... Each person rolled, and if the majority succeeded, than the group succeeded (and helped Blackjack/Trinia along). If the majority failed, than the group failed and suffered some consequence.
So in one instance, some had failed their acrobatics to scramble up a steep roof and so they slipped down, but were caught by another person, who helped them up the rest of the way--the one had 'failed' but the group had succeeded over all. In another instance, they had to stealth past a Hellknight patrol. All but one succeeded with flying colors--the last one had a nat-1. So that person bumped into something and caused a clatter, but that clatter happened the same time a bigger noise happened just down the road, so the Hellknight went towards the bigger noise, letting the group get away successfully.
Once they got to the docks, Blackjack had a boat he could use to get himself and Trinia out of the city, and he thanked them for their help. They determined Trinia had an illusion spell and some sort of enchantment on her, and asked if Blackjack could let them know (via their mutual friend) who this woman is and what happens to her. He promised to do so, and they part ways.
[Meanwhile, one of my players is playing an old man dwarf, not well suited for scrambling through tunnels or rooftops, and he stayed behind to watch their backs, then went to a bar to find out what people were saying about what happened, and I was able to jump back and forth between the scenes, giving the dwarf information about things while the others did the running around]
I think I needed to have some guards chasing them more overtly, to give more urgency to the chase, but I'm not great at juggling several things, and well, hindsight is 20/20 after all. Still, I think it went pretty well and my players seemed to have a lot of fun with it. so, yay!
