Here's the Assassins crew sheet so you can follow along at home.
In addition to doing murder jobs for Lady Kinclaith and others, the crew will also do scores to seize their Claims, too. You can see the claims roadmap for the crew on the left side of the sheet (the gray boxes with lines connecting them).
When you say 'roadmap' does that mean there is a certain order they need to follow when getting these claims?
Also the Vice Den claim, if they were to get say a gambling den would that mean the Catterby could start making coin from here vice?
It's more like a claim tree rather than a roadmap. You can choose different paths, but they are paths. Although they do intersect at different points.