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I grabbed a lifetime pass for $99 many years ago and have certainly gotten my moneys worth. Hopefully they will keep honoring existing passes.
I cannot fathom why you'd pay $750 for Plex when Jellyfin is free.
I mean, that's probably what it is, a last squeeze while something somewhat remains of their Plex brand image, knowing the war to Jellyfin is over and lost. At that rate, Jellyfin could start a commercial entity, partner up with mullvad or whoever, and offer a STUN/TURN proxy service that they could charge cents/dollars a year and still make bank.
Have you used Jellyfin’s clients? I’ll be the first in line to complain about some issues with the Plex client [0] but it’s been remarkably stable over the decade+ I’ve used it. I did not enjoy the Jellyfin clients (or lack there of for some platforms) the last time I tried them (2-3 years ago).

The Plex client, for all its warts, is much more user-friendly IMHO for the friends/family that might use one’s media server.

[0] I could go on and on about things like how shitty Plex is for downloading content to your phone/iPad to take on a plane/offline.

They didn't have to become yet another second-rate streaming and rental platform. They could have remained the best home media server.
Can someone explain the advantage of Plex over Stremio + TB + AIOStreams to me?
For me it's that Xbox has a Plex app. I'm not willing to use Android TV devices or connect my TV to the internet.
The UX of Plex is unbeatable, there are no obvious signs that the content is pirated, that + a great app ecosystem is very important if you're going to be sharing with friends and family.