If it was just my parents and I using it, that’d be fine, but it’s not. In my experience, nothing is quite as simple as “always on”, and if something breaks, even unrelated to tailscale or anything I set up, I’ll be to blame even when it wasn’t my fault.

It just wouldn’t work for my users, unfortunately, and I don’t want to be responsible for endpoints not on networks I own. I’m not denying that it’s possible or that it works for some people.

That’s the real benefit of a solution like Plex - it makes it so I only have to manage my own network, and if I want to invite someone new, I just ask them for the email attached to their Plex account, and I’m done.

I also am curious where you’re finding rpi’s for $35.