Yes, stropping is an "art", more than a skill.... it takes time to learn the "feel", never mind figuring it all out.
Here's a link to Liam Finnigans stropping at the Waldorf barber shop... if you ask me, he uses his strop "scary" slack, but it works for him!
Most of my strops are too stiff to strop like that, but my dads barber chair strop (back from the 50s and 60s in his shop), has the same "rubbery" look.
I would not recommend anyone use as slack a strop as Liam does, but I do feel it shows that one must not pull the strop *tight*, but rather just pull it enough so that it doesn't flop about. Light to no pressure on the razor, any pressure there is, should be on the spine, not the edge. The edge should just come along for the ride.... gliding on the leather. If the leather deflects at all, it should ONLY be at the spine, never at the edge.
Still, for those of you with a brave heart, here's Liam stropping one of his razors before shaving a customer.
https://www.youtube.com/watch?v=2h1GC34yyKE