Fortunately, Critical Fails aren't a thing in 5E. And I don't remember our GM instituting a Critical Fail houserule... although it has been a while so I suppose I could be mistaken.
True.
But Ikar's crew seem to be out to get us - and them. An alliance with the frey Dogs could be useful.
Lali would like to make friends with them because they have experience in going deeper into the Mournland, but she will not object if someone tries to make Kalli pay us.
37 wouldn't think this way, but as a player I see helping Kalli as a boon we can call in later. Maybe it's my history in the WoD games, but someone owing you a favor is usually worth more than money.
Did we talk at all about our past adventures with Earic and the airship that we need soarwood to fix. I don't want to repeat it, but I can give a quick summary in-character.
Ok. So Kalazart is important as a potential spot to scavenge soarwood to repair your sentient airship friend. And it's also the location of the professor's mysterious other workshop.
No-one can find that city, but our goblin friend may know someone who has mapped a path there? Is that Windchaser?
Is the professor by any chance also the kind of colossi expert that would be needed for the repairs?
The Professor... it didn't really come up whether he knows anything about colossi. Although, having read his notes, 37 or Tryne could roll me an investigation check to find out.
On second thought, Tryne has specifically read about docents in the professor's notes and is currently on the hunt for one. He already knows that they were used in Collossi construction. For Tryne, he would have a pretty good idea that the professor has some experience in this matter.