Cool concept (especially since NV, unlike other purportedly Fallout-related titles I do not care to name, actually provides a believable socioeconomic basis for a slave trade), so no offense intended here, but since you seem to be a bit into RPing these characters (or at least giving them interesting backstories): How do you rationalize Boone (of all the companions, especially Boone) helping you along in this endeavor rather than, say, shooting you in the neck and groin and setting your livestock loose?
(Also out of curiosity: this guy doesn't happen to have taken the Cannibal perk too, does he?)