I think that what blows the minds of cigar to pipe transition guys, is that there is a whole world of tobacco flavors that they have barely ever even touched by sticking to cigars. Cigar snobs tend to prefer a taste range that is kept close to the Cuban examples of fermented burley. This means that almost every cigar (without flavorings) in a cigar shop only varies a degree or two in taste from the Connecticut to Maduro. But, when you turn to pipes, and add in Virginias, Dark Fired KY, Latakia, perique, they have to open their minds. It's like going from only seeing the color blue to seeing every color of the rainbow. Some of them can't handle it, because they've dug themselves into the cigar snob hole for flavor.
My suggestion to cigar guys is to open their minds to what tobacco can taste like, and try them all swim in the varieties. There is no Cuban altar to false gods in the pipe world. You are free to like anything. In a cigar, most of the flavor comes from the lips touching the wrap. If they are stuck in the mind numbingly stupid idea of Cubans being the pinnacle of flavor, then, just drop the idea. They'd never enjoy the pipe.