Let Jed Masterson know you are ready to leave once you are traveling alone and carrying ≤75 pounds of gear.
The weight limit can be increased to 100 pounds by using the Strong Back or Pack Rat perks, or passing a Survival check of 50 with Masterson.
Ricky can be convinced to carry some of the Courier's gear (also raising the limit to 100 pounds) by passing multiple dialogue checks (Survival, Guns, Science and Speech) with him and convincing him to carry some gear instead of exposing Ricky's lies.
Find the Happy Trails caravan master.
Let Jed Masterson know you're ready to leave once you're traveling alone and carrying 75 pounds or less.
Let Jed Masterson know you're ready to leave once you're traveling alone and carrying 100 pounds or less.
When you start this side-quest, you will not lose any of your gear. You will only be allowed to carry 100 pounds or less, while having a crate nearby that you can use to store any extra equipment.
You cannot kill or even hurt any of the non-player characters within the Northern Passage; attacking them has no effect, nor will they turn hostile.
This quest marks the only time you have a weight limit when traveling to or from Zion. After the add-on is complete, the trip can be made with as many items in your inventory as you please because there will not be a weight limit.
If you make Ricky leave, he will be replaced by another guard with a hunting rifle.
If you make Ricky leave after telling him to carry some of your items you will still be able to carry the extra weight.
When you first talk to Jed and you have killed everyone with Cass during the Heartache by the Number quest (or even simply Alice McLafferty), he will say "Hang on- aren't you the one that wiped out the Crimson Caravan's Vegas branch not too long ago?"
Alternatively, when you first talk to Jed and you have completed side quests for Crimson Caravan and have not killed everyone at the Vegas Crimson Caravan branch, Jed will say "Wait a minute I recognize you. Yeah... you're Alice McLafferty's rising star, aren't you."