Selfhosted
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Very easy server-wise. But you may neeed to help your family member/friend with the initial set up on the client, if they are not so tech-savy.
A big PSA here is to have them pass you the device activation link that pops up when they first start Tailscale, and activate their device on your tailnet.
Then you tag it, write an ACL rule for it (or you probably already have a rule for Jellyfin clients connecting only to the Jellyfin server on your tailnet by now, so just the tagging is enough) and that's it.
MUCH simpler than having non-savvy people attempt to set up a Tailscale user account. Plus, you can only have 6 users in a free tailnet but you can have 100 devices.