At my job if we put encrypt in an email message the server encrypts it before sending maybe he thought it was like that

Plex actively removes features though that hasn’t happened and like other comments says it’s easy to move away in this case

That’s almost my same exact setup. Pc parts in my house currently go me --> son —> server. Servers got the ole trusty launch 1700 still going.

Tailscale is amazing. When i first started self hosting i tried a bunch of things to avoid a companies solution but tailscale just works perfectly and form what they say in interviews they dont intend to change the free tiers. Its also open source and there’s headscale so eventually you could not rely on the company at all.