Following Chapter One of Waterdeep Dragon Heist, my players had some treasure, and the keys to Trollskull Manor. My focus for Chapter Two of the module was renovating the manor, and completing some faction missions. Overall, we spent five sessions in this chapter, but the module is flexible enough that we could have spent much longer than that.
Trollskull Manor was an important element of my WDH campaign, it helped tie the characters to the city of Waterdeep, and became a very useful tool as a DM to motivate my players. In WDH, before the manor can be opened it first needs to be renovated, which requires a hefty sum of gold for level two characters. Thankfully the module puts a decent amount of treasure in Chapter One that can be sold to raise funds, I allowed any remaining costs to be covered by a loan from the Fellowship of Innkeepers. My main way to motivate renovating the tavern was Frewn and his rival tavern, who my players quickly learned to hate. In my campaign, I had Frewn’s tavern be under renovation as well, and my players had to race Frewn to open their tavern first.
My other focus for Chapter Two was getting the players introduced to some factions, in my campaign the main faction my players worked with were the Harpers. I would recommend reading the “Factions in Waterdeep” section of the Introduction and only including factions that would approach the party, instead of trying to use all the factions. I would also suggest picking up the Waterdeep: Expanded Faction Missions PDF on DMs Guild, it really helped me to flesh out the faction missions in the book, which are a little underdeveloped in my opinion.
In my experience Chapter Two was the most fun as a sandbox, I frequently gave my players several options at once and let them follow up on whatever sounded the most fun. One strategy I used to ensure my players always had new things to do was introducing an NPC presented in Chapter Two: Ulkoria Stonemarrow, a member of the Watchful Order of Magists and Protectors with ties to Trollskull Manor. I used Ulkoria to hand out any missions that I was interested in running from the factions that never introduced themselves to the party. Finally, I expanded Chapter Two by adding the Faction Outpost from The Alexandrian Remix for my chosen villain, The Cassalanters. While I decided not to run the remix, I found that it was a good source to take ideas from such as the outposts.
We ended our Chapter Two experience with the opening of Trollskull Manor, which I found fun to run as a skill challenge. With my two goals for the chapter complete, I felt we were ready to move onto the next chapter, so the following morning my party woke up to a fireball.