Earlier quoted context omitted.
I think you overestimate the technical capabilities of my family or their eagerness to install software. When I ran Plex, and nobody ever installed the Plex app like I recommended to them, even though it's one click away in all the app stores.
I mean, if they aren't even willing to download the one app that actually gets them the content they want to see, then *no* software will ever be something that this type of user will be interested in. Not everyone has to use an app, so why try and cater to an audience who clearly has zero interest? You're not gonna magically make it somehow even easier than "go to app store, download app" to the point that they'll u…
Tailscale is exponentially worse, though. Not only would I have ask them to go to Jellyfin and sign up and log in, I would have to explain that they can't do that until they've installed the Tailscale app (which I have to explain because most non-techies do not know what a VPN is). Tailscale requires its own account, so they have to first sign up to that, and I have to add them as an external user first.