You Can Depend on Me
You can start this quest by speaking to Alice McLafferty inside of the Crimson Caravan Company Main Office. Ask her for some work to find out she needs someone to do her running. Head to Camp McCarran and find Hildern in his office. Make the delivery and return to Alice. Ask her about all the jobs to limit going back and forth with her all the time. Head to the Mojave Outpost in the south west corner of the map to find Cass in the barracks drinking. Convince her to sell Cassidy Caravans with either of the challenges (requiring 50/75 Barter or Speech depending on your choices). If you choose the Speech 50 option you gain the quest "Heartache by the Number" and must work with Ranger Jackson, the other options let you recruit Cass right away. Return to Alice with Cass alive to receive [500 CAPS] and NCR Fame.
Henry Jamison is the next objective and you can find him at the Atomic Wrangler in Freeside. The task is simple enough with a Speech skill of 50 , a simple challenge will make him resign his position. Otherwise you have to kill him or pay him a severance. Return to Alice to tell the good news, you are rewarded with [150 CAPS] if you kill Henry, [300 CAPS] if you paid his debt and gave him severance, [400 CAPS] if you only paid his debt, or [500 CAPS] if you convinced him to quit with the Speech challenge; you also receive Crimson Caravan Fame.
There is more than one path to success
Next up is the Gun Runners facility so head there. The only way through the gated area is to pick the lock so do so when no one is looking then dart for the building. Once here sneak your way straight back and use the computer along the right side and choose "Download manufacturing specifications" to complete the objective. Return to Alice to receive [300 CAPS] if you shot someone or they shot you, or [500 CAPS] if you weren't seen, as well as Crimson Caravan Fame. After all the quests are done you receive [500 EXPERIENCE POINTS].