I think when trying to orange pill someone, we often start with the solution, which most are not ready to hear because it's such a phase shift. I find starting at first principles and asking undeniable questions like 'if technology replaces labour, why do things continue to get more expensive?' tend to lead to a greater discussion. 

 Sure, but depending on the programming that person has received, they might have bought the "corporate greed" line or something else. Takes work to undo the statism... 

 Spot on. My should-I-orange-pill-them formula is…

Degree of             Time needed
influence      X      to deprogram
on my life               this person
———————————————
Opportunity cost 
of that “time required”