Pardon my ignorance but HTTPS certs can be middle manned? Could you give me a TLDR of how if you got some time?

Not a contributing comment but just wanted to say:

THIS IS THE WAY

For those that needed to hear that.

Personally, I run the following:

Hardware:

• Mini PC (beelink but used to use raspberry pi)
• 1tb external drive for now

Software/OS

• proxmox (so I can virtuaize what I Host on one machine)
• Ubuntu server in a VM
• jellyfin (media server)
• tailscale (to access my server from anywhere)

One of the top comments mentions starting with plex. I also recommend that. Jellyfin is cool but plex makes a lot of features such as sharing and subtitles much easier. You also can with jellyfin but it’s much more technical. The only reason I went away from it was I felt the direction plex was going seemed a little too commercial for me. And I also like to use open source when I can.