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Selfhosted
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Stay away from Plex, if you like to go with Free and Open source.
I'll start with Jellyfin, and Arr family (sonarr,radarr,prowlarr or Jackett), Vaultwarden and immich
Edit: Learn to spin up docker instances first, as above services would be easier to manage in docker containers and for back ups I prefer Duplicati. And if you run it 24x7 add AdguardHome or PiHole to the mix
Edit1: if you are extremely new to docker instances and find it hard to learn, just spin up CasaOS and you'll be good to go as it makes spinning up docker containers so easy.
Plex is a far better and user friendly version than jellyfin or emby in my experience especially if you want to share to friends. Granted it's not open source and has gone commercial route so there is the risk it will continue there. But for now I wouldn't push to move. If jellyfin can get some more app support and continue to develop and be ready for when Plex messes up then it will take off.
Not if they need their own Plex Pass for so many features. The only thing Jellyfin lacks is user self password resets and transcoded downloads. I don't really see any other advantages in Plex
Transcoded downloads are a pretty big deal unless you want to stream 4K blue ray HDR to your iPhone.
Downloads, not streaming.