Friends and family are nice. In my experience they react like "wow amazing, how much you pay for that?" But they actually mean "wtf dude you never heard of netflix?" (:

I set up everything behind Authentik SSO so that, when they ask me to set them up with jellyfin to watch movies & tv, they suddenly have access to a whole suite of tools. That way, they can explore on their own and decide - which seems to work well. Not sure what kind of users you have, but mine are very quick to ring me up when something is not working!

I'm quite terrible at keeping up with folks, and so I find these support calls to be a great way to keep in touch actually! But I could definitely see it getting annoying too.

As much as I like fully self hosting, I ended up paying for Plex lifetime and have it running in docker. It was $120, but has already paid for itself twice over since I managed to convince my wife to drop hbo max, Netflix, and a couple others. She isn't technical at all so she was hesitant, but she likes plex. If she can't find what she wants to watch on our few streaming services (paid for by our cell provider, otherwise they'd be cancelled too), she can add it to the watchlist on Plex and radarr or sonarr will download it automatically and make it available on plex pretty quickly (or she'll tell me to get it and let her know when it's done).

I could open my Plex server to more family or friends, but most of them either pirate stuff themselves or are fine with paying for streaming services for the ease of use.