The problem is the "lifetime" option, they needed to just stop offering it.
The optics of making it prohibitively expensive instead is just terrible.
It used to "pay for itself" after 3.5 years, now it takes over a decade. I don't think they understand most people were buying it before (as in a decade ago) as a form of donation to a software that didn't have a good alternative.
Now that Plex is trying to become a media streamer themselves for a revenue stream, and alternatives like jellyfin exist for what made Plex popular....
They should have just sunset the "lifetime" deal