| There is historical fact, and then there is the question of how you want to shape historical fact into your campaign.
Historically, there are a lot of options. Weregild, a saxon and nordic concept, is as Rhialto so ably describes (though I think he is historically off base a little with the guild court). Later courts used different concept, but there has been a wrongful death concept applied to employers in every legal system I know of. Here is the significance: weregild is paid under any circumstance. Death means payment, period (lawyers call this strict liability nowadays). Later courts (but still in the Middle Ages) applied the idea of negligence, i.e., were the players acting with reasonable care, and if so, no liability. Finally, there is the concept of fraud upon the apprentice's master. Probably the master has to pay an indemnity to the boy's parents if the boy dies. He would certainly try to collect this indemnity from the players.
You might also distinguish between the criminal liability and the civil liability, though I don't think this concept developed until at least the Renaissance. No data there.
Medieval cities were usually chartered by the crown (to get them out of the feudal system that would otherwise control the city land), and had city courts. Churches had their own legal system, but I don't think guilds did.
I'd suggest your cartographer sues for an indemnity (against his weregild) and for damages to his business (no helper). The city magistrates question whether the boy's death was due to the negligence of the PCs, in which case they go to jail.
In a courtroom, other adventurers come in to present evidence that the marching order was poorly thought out, the equipment was inadequate for umber hulks, etc. The PCs have to defend their tactics, which is actually quite cool. Always arrange to have them bribed out by a crimelord or rescued by someone in a dramatic battle if necessary.
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