Have to admit, quite impressive that someone is still paying this much for Plex given the free alternative like Jellyfin that can do pretty much everything the same.
What’s the psychology here that people are willing to pay this much for this software, yet not even $20 for another?
It's pretty slick looking which is worth something to me. Not $750, but something. But even though some of the UX choices of Jellyfin didn't make sense to me, it's an amazing piece of software, so I'm sticking with that, and using Wholphin [1] as a frontend.
I have a lifetime pass I bought many years ago for not much money, Plex had apps in all Platforms. Jellyfin does not at this point, even though there’s work being done everywhere.
Plex just works and is supporter everywhere. Not that surprising that people use it.
What information do you have that people are actually paying this price?
There are plenty of situations where a business must charge over X for one reason and must charge under Y for another, where Y < X. What happens is generally they go for the "over X" branch for fairly obvious reasons, then go out of business sooner or later because they can't actually charge that. Just the fact that they are trying to charge that much doesn't mean people are paying it.