One major paint point for me is their policy concerning the mobile app. I paid for the lifetime pass for my account with the goal that Plex would work well for my users and myself.

This is not the case anymore since now users need to pay to be able to use the mobile app to stream from my server, otherwise they're limited to 5 minutes.

I ended up making a small web UI where they can log in, search for movies and episodes, and download them.

Why? Why do my users have to pay to stream from my server?

No, I paid for a lifetime license to an application that didn't have ads, didn't collect viewing data (and email it to my friends!), and wasn't blocking people hosting Plex wherever they want.

If you can find a company that went from simply paying for a license to incorporating data collection, advertising, and raised VC funds and became better after, I'd love to hear about it.