There’s some cool stuff here, but I feel like it still needs a bit of further consolidation and simplification in order to create a tighter product. I’m gonna offer some hack and slash editing feedback, so feel free to take or leave bits and pieces of what I say as you like.
Healers’ Guild
I don’t think this guild brings much to the table as a major guild in Dragonwick. They don’t fit thematically, because our major themes of the Dragonwick guilds are Wealth, Commerce, Craftsmanship, Resource Exploitation, Corporatism, and Dragons. I think they can be eliminated or made a minor guild in the background.
I do like a 4-Guild superstructure to the town though. So what could take this slot as the 4th major guild?
Temple of the Crossroads
Another reason to eliminate the healers as a major is so we don’t have two competing churches in the city. I think having multiple prominent religious orders in a city that’s all about Commerce detracts from the central theme. Then, I would make the title of the leader of the gambling-church "Banker-Cleric" or something. Arch-Broker and his Actuary-Priests. Notary-Acolytes who collect Ante-tithes.
Renderer’s Guild
I like this simplification down to 4 major guilds. I think you could even fold the Armorers, Weaponsmiths, Tanners, (and Arsonists?) as subsets of the dragon rendering cartel? Actually, maybe "Renderer’s Cartel" would be a nice title for that Guild? This set of craftsmen and businessmen is kind of the heart of dragonwick’s industrial park.
Penwright’s Guild
I’m also having a hard time fitting this new addition into the overall structure of the guilds. I could imagine creating a complementary Major Cartel that is composed of the Temple of the Crossroads (Gambling), and the Bankers’ Guild. I’m imagining the Penwrights as producers of pens that all of the bankers, merchants, and debt collectors use in their ledgers. Rather than just memorizing what the pens write, maybe they actually transcribe everything into a secret secured ledger held by the Penwright Guild! I’m imagining they’ve effectively created a blockchain, distributed trust network for this little libertarian paradise! They could be the central arbiters who resolve any disputes, validate debts, etc. Obviously this is all sensitive information, so they hold the master ledger in an secured vault.
In this way, they wouldn’t be stealing personal secrets wholesale — but certainly the ability to follow The money in the city tells them a lot about the secrets of the rest of the guildmasters of this city and gives them enormous power and leverage. Nonetheless, other Guild-leaders use their pens, because carrying such a pen allows you to carry out official transactions anytime and anyplace. You can travel abroad procuring goods, and carry out secure transactions in the master ledger without the risk or inconvenience of carrying cartfuls of gold! International banking at its best (and worst)! This would also tie the Penwrights back to some central themes of Dragonwick: Commerce, Libertarianism, and Power.
Kobold Hutches
Where are you imagining these? Outside of the city? I have a hard time seeing kobolds wanting to be part of a society that makes its living off hunting & harvesting dragons. But I think kobolds will come into play plenty as adventurers get out and hunt actual dragons. Maybe there are some kobold dens that hold information on the whereabouts of dragons, that lower level adventurers can assault to bring back dragon information?
You know, it just occurred to me how very much the Guild Leaders are like the hoarding dragons that they hunt...
Anyway, those are the ideas I’m throwing at the wall. Obviously this is your brainchild, so you have veto power on anything hat doesn’t jive with your vision. I’m trying to offer bolder input, on the assumption that you’ll use your veto aggressively on anything that doesn’t jive. But I think we’ve got a lot of ideas here now, and some bolder editing and reworking will create a more robust final product.
Do you have a google doc for Dragonwick? It might be time to graduate to that format, for the sake of being able to structure things clearly and edit easily.