Yes indeed <a contenteditable="false" data-ipshover="" data-ipshover-target="<___base_url___>/index.php?/profile/18037-banishedused/&do=hovercard" data-mentionid="18037" href="<___base_url___>/index.php?/profile/18037-banishedused/">@
banished&Used</a>, that's quite some debt you got! Still, with a Melting House producing Pfennigs it should get paid off fairly quickly and your experience confirms what I was seeing in my settlement.
What I am wondering now, is how much of any given resource will the Bootleggers supply? I am pretty sure that
what they supply is determined by a random chart and I have seen my own Bootlegger supply the more expensive clothes so I know that they will supply some expensive items but that doesn't indicate how many items they would supply. My bootlegger stopped supplying anything at just -2 Pfennigs but one of yours let the debt get to -500.
If nothing else it shows just how much variation is possible between games. To clarify that statement, my town also had a population of around 430 adults but a student population of about 30 and a child population of approximately 60 so it's somewhat similar to yours. However I have a much greater food reserve at the moment (around 110,000 units stored) and my other resources are stored almost to the limits that I have set for them. So... that makes me wonder if the Bootlegger is more active than simply just supplying some random resource?
I don't make use of the Bootlegger or Smuggler that much, I often have just one example of each and I build them after the town's food supply is well taken care of. So what I am thinking now is "Does the Bootlegger supply more resources to a town that has very few of a given resource?" That is to say, does the Bootlegger (and Smuggler) react to the quantities of resources you have in storage and if you don't have many, does it supply a larger amount? That's about the only explanation I can think of for your town owing the Bootlegger so much money before it stopped supplying anything where as my Bootlegger was only supplying small amounts and stopped delivering anything when I reached -2 Pfennigs.
Again, I'd love to hear what the <abbr title="Colonial Charter">CC</abbr> devs have to say about this. If the Bootlegger & Smuggler supply more resources when a town is resource poor and then slow down the amount of resources supplied if the town has an abundance of that resource, it's a really great mechanic and a fantastic example of how creative & clever the Modders can be.