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Did you notice what you said there each major version. Plex has been rolling releases for years. Maybe they should have done Plex 1 2 etc. yes software has been that way forever but you would pay for a version and then a year later pay for another one. Now people expect to pay once and get upgrades forever.
Because they're called "lifetime passes" voluntarily offered by the company. It seems weird to act like people are being entitled about this or that their $75-$120 one-time payment is meaningless compared to someone who's only paid $5 or worse using it for free.
Sure, I'm not saying Plex has to do a single-payment model. Just that it's a think that's been done successfully (and for longer than Plex has existed). Everyone's pushing subscription models so hard that it's easy to think "this is the only possible way that anything can work".