I like to smoke during some kind of activity like golfing, walking around the neighborhood, being around the farm shooting guns, etc. If one of those things are going on then Im going to smoke for the duration. Halfway through the 2nd one its hard for me to taste anything but I dont waste a good cigar.
Another scenario where I will smoke more than one is when I get a bad stick or smoke one thats not quite "ready." I try to give it a full third, but after that I throw it away and go for another.
These times are few and far between so if the opportunity presents itself for more than one Im all in.