Take the evidence of the Caravan attacks to Jackson at the Mojave Outpost. These pieces of evidence are in the safes in the offices of the Crimson Caravan company ( Crimson Caravan - Van Graff agreement) and the Silver Rush ( Letter to Gloria).
Track down Durable Dunn's missing caravan with Cass.Investigate the wreckage of the Griffin Wares Caravan with Cass.Pay your respects with Cass at her caravan's grave.Talk to her about what she wants to do next.With a Speech of 75, the Courier can just challenge her by telling her she's responsible for the destruction of her caravan, and she'll reluctantly agree.Complete the quest Can You Find it in Your Heart? or kill Jackson to get her to leave. Cass will agree, but will point out that Ranger Jackson won't let her leave.
With a Speech of 50, the Courier can suggest that the Outpost is a pretty terrible place to be trapped.This requires 12 bottles of whiskeys and return to Cass. With a Barter of 75, the Courier can challenge her to a drinking contest.With a Barter of 50, the Courier can choose to sweeten the deal by throwing in an extra 750 caps.Return to Cass and convince her to part with the title for Cassidy Caravans.Begin You Can Depend on Me and continue that quest until given the task of convincing Cass to part with Cassidy Caravans.Rose of Sharon Cassidy came to the Mojave with her caravan, but that dream has fallen through, run out of business by her competitors.