I've tried Caravan against Ringo and the bartender at the Mojave Outpost, and it was completely confusing. I lost both times. Thankfully it was a minuscule amount of caps, but it's something I really want to learn to do and it's really, really difficult from what I've done. >.<
[8:32:45 PM] Dusty Lens: Oh no, let me get that. Hello? Oh it's my grandma. She says to be roleplay.
[12:49:19 AM] Elgatodiablo: You know its nice that you have all that proof and all, Bacon... but I just don't believe you.
I'm trying to find another entrance to the strip, 'cause if i try the freeside one it crashes.
D:
Also: Caravan = Wut?
The Monorail is inside Camp McCarren. Make sure your rep with the NCR is "liked" otherwise the NPC's guarding the Monorail will shoot at you if you try to go near the door. (I almost forgot, you can get NCR Armour and wear it while disguised and be able to go through I think.)
Also, Caravan. I hate it. Too slow paced and low stakes, I prefer Blackjack with 7-9 Luck and betting 200 Chips at a time. Made so much money that way, it was beautiful.