First, sorry for the late answer, but there has been a lot...
I'll try to explain my own way of preparing and how this ould be translated into a Cadwallon game.
I love to build sandboxes for my games and put a lot of effort into background and NPC building, probably way more material than my players will ever explore and find out about. I did this for all my major games: Das Schwarze Auge (Realms of Arkania / The Dark Eye, a classic EDO-fantasy setting and germany's most poular as well), Shadowrun and both Vampire: The Masquerade and Vampire: The Requiem.
I started this with Masquerade and had way to much NPCs, way to many maps and way to less plot hooks between the NPCs and the PCs. This evolved with Requiem. I again came up with a fictional city, where the game happened and with a lot of NPCs. But this time, every NPC had to have at least three connections to another NPC, may it be that the are rivals, lovers, secret helpers, some sort of godfather, whatever. So when the PC befriended one NPC or annoyed another one, it had direct influences on how the other NPCs may changed their behaviour towards the PC.
This is sure best fitted for a game of intrigues like Vampire is, but it works to a certain level for other games as well.
As for our fantasy-setting, the PCs have been in a mercenary group that was settled in an old fortress with a small village. The other mercenaries and the villagers alone gave many plothooks for the players, there have been plots in every direction they looked, they just needed to talk to the people. Everyone had a few sentences about their character and motivations and I heavily dug up deviantart for interesting pictures for them. And then there have been the usual contracts as they were mercenaries. Kind of similar to Dogs of War... There was th greater region where the game took place with all the cities and settlements, and because the game as a huge and well-written background, I did not need to dig that much deep, it has been already there.
For Shadowrun, I had a similar approach. We play in Berlin, and there exist excellent background material, so I came up with an neighbourhood of my own, wrote again some NPCs with short desriptions and of course a picture, had some interesting locations and tried to find something interesting for every NPC.
For Cadwallon, I'd go pretty much the same way. To make things easier, I'd suggest your PCs are all from the same fiefdom. Then, look a the NPC section and find the already written NPCs for that fiefdom. The description for the fiefdom alone is so rich and detailed and gives a lot of ideas. As some sort of inspiration, I'll have a look at two of them, one upper city and one lower city.
SomaFirst thing that pops up in the Plot part of the description is the vendetta between the Somas and the Usurers, but this is something for the long run and could come in handy from time to time.
The port of Ondine gives great opportunities for anything related with smuggle (Guild of Ferryman included), as the Militia tends to look away. The slums with their crimes give other options.
Cadwallon's only magic school is here, further the Guild of Thieves and the Embassy of Alahan!
First, design a meeting place, ideally an Inn or somewhere else, where the PC are often and regularly. The keeper might be a former Free Leaguer himself with some dark secrets or troubles that haunt him and will get to him eventually. Then just go for a bit of the neighbourhood, where the PCs live. Maybe a shop, maybe an orphanage, maybe a healer. Maybe someone from the magic school, it might either go into the direction of Ankh-Morpork for more laughter or in a more serious direction if you chose someone like Snape as a role modell. However, fill the street with some life. There could be someone who works in the harbour who can give informations or get into trouble.
The more NPCs you have that you PCs have connections to, the easier is it to draw them into a plot with personal involvement.
A few quick ideas for some plots:
• Something was stolen fom the Inn, although the keeper had a contract with the Guild of Thieves. The PCs have to investigate in the guild to find the one who did this, ideally without handing the suspect to the guild. maybe he just did not know what he did.
• Someone from the magic school waits for urgently needed ingredients, but they did not show up in the harbour. The PCs find out, that some gang from the Slums snatched it away and they have to retrieve it.
• Later they might find out, that the magician is from the Soma family and the gang was hired by the Usurers.
• Someone in the Embassy needs help, but it has to be discret and swift. Maybe a secret negotiation with an unusual ally?
• As always, you can go for some dungeon exploring in the underground.
• Even going to another realm in the magic school could be possible!
Var-Nokkt
This mostly dwarven fiefdom is run like a guild and the ruling familiy acts like in a guild. They have heavy connections to the Guild of Goldsmiths (and therefore the Howling Pack, the Wolfen Clan Box, can be included as well
). With the strong connections to Tir-Na-Bor, anything related to them could be relevant to the fiefdom as well. This fiefdom is in struggle with the fiefdom of Drakaer, with the Ogre family of the Orrkrks standing between them, as they are friends with both. So this fiefdom is more open to intrigue and political conflict.
The same as above concerning the NPC-connections has to be considerer, but fitting to the dwarven style of the fiefdom.
Some plot ideas:
• A famous dressmaker needs some ingredients, this might be silk from enormous spiders or some rare flowers for colouring his cloth. This dressmaker later could provide fancy dresses for the PCs, when they are going to a social evening of the Var-Nokkt family, where they are drawn into the intrigues and conflicts between the families and fiefdoms. Maybe an attempted assassination and the PCs are the suspects and have to find the true culprit to clear their name?
• The barracks with their internal struggle could be an opportunity for sime undercover work disguised as militia.
• During a dungeon exploration, the group stumbles across a strange automaton. Luckily, Yeoneul the Heliaia is willing to study and repair that construct. Unfortunately, it is caught in a rampage-mode-loop and runs amok as soon as activated.
• There could be problems in the sewers and the crand canal of Shû-Az that need a free league to solve.
In general, I think the books are very detailed to give some starting points. Together with some interesting NPCs, who have connections to other fiefdoms or NPCs of importance or troubles in their past, a feeling for the district and a personal connection towards the NPCs, your players should be easily affected or engaged with them to find not only Ducat motivation, but personal and emotional motivation as well.