It also means you end up playing administrator to all of the “I forgot my password for the ninth time this week, can you reset it for me” inane requests.

Jellyfin is a self-hosted streaming service. You have just understood the concept of self-hosting, Sir.

your only real option for remote access is a VPN. But that makes sharing with friends/family extremely difficult.

The first part is true. The latter is exaggerated. Yes, it’s more if a hassle than just “install the app, follow a link and you’re done.” That said, if done through wg-easy (a wireguard configuration frontend), it’s “install two apps, scan a QR code, enter a server URL and you’re done.” Also, corporations spoon-feeding users, creating an expectation that tech just magically knows who I am and works on fairydust and rainbows, that’s what got us into this mess. Expecting a modicum of setting up from the user isn’t too much to ask if they can then access somebody else’s services for free.