Chewy7324

Especially anime often use the superior .ass subtitle format, which many devices don't support. Sadly Crunchyroll is switching to .srt which has broader support, so it likely won't require burning them in the video (transcoding), which is the only positive thing (still a shame imo).

https://www.reddit.com/r/anime/comments/1nuxuzs/crunchyroll_has_downgraded_their_subtitles

Given they use a N100, I'd suggest redownloading instead of transcoding for time, energy and quality savings (i.e cost).

And making sure Tailscale auto launches on a FireTV stick is a pita too. Telling them to open Tailscale on each start is not an option.

Setting up auth before Jellyfin breaks clients. This is not an option. Edit: Unless you meant VPN like Tailscale, but then you'd have to install Tailscale too, which I don't want to explain to others.

And sharing my libraries with other friends sharing back with me is pretty great.

This feature is imo THE killer feature of Plex, although I use Jellyfin. There's no sharing of libraries like Plex does. Multiple user accounts per server, yes, but you have to switch between servers and search separately.