I watched this a couple of days ago. I really enjoyed his talk. Sometimes I feel like I’m talking crazy pills with what people put up with in UI. All his points made total sense to me.

I would not update to windows 11. I installed Bazzite and Jellyfin was a one click install. Plex was more involved. Plus Plex seems to be well on its way to enshitification.

I haven’t set this up myself as my internet provider doesn’t do a public IP address per customer. I never even corrected it with plex.

But as far as I’ve heard, the difficult part is setting it up on the host side with tailscale. From your dad’s side, it should just be entering your IP and then the user/password.

• I don’t see anything in settings or in the official plugins but there seems to be some plugins. Some seem to be to just search and not the pre-roll trailers.
• There is a subtitles plugin that works well. It is not as cleanly handled for my tastes. You have to search for it on the media landing page. You cannot download and select while playing your media.
• You can filter and then sort
• I do not have experience to answer that
• There is a delete media option. I am transferring a large amount of data right now and cannot test if it deletes it from Jellyfin or entirely.

I used Plex, and have a lifetime account, for the past decade. I just switched over to Jellyfin this week.

Feel free to ask any questions that you have about differences or my opinion.