Plex can be amazing, but the core user community has absolutely no idea what the heck the Plex devs are doing these days. I've almost never seen such a disconnect between product development and key user community. /r/plex is basically full of posts complaining about long-standing requests, bugs, and broken features that are just simply ignore, followed by posts of "plex just released new feature literally nobody is asking for or wants, wtf?"
Most of the WTF feature releases are rolled back or deprecated within a few releases. So the community tends to be right on with what Plex should be doing. There's a lot of pigheadedness on the engineering side it looks like.
I also agree the lifetime pass was a bad business move. I think a better model would have been something like "pay $45, get every release in this major version, new major versions come out approximately every year" or with an alternate tier that would be "use plex, pay $35 per year, get all the updates". It would have smoothed out revenue and focused development on paying customer demands.