I like 5, 1 and 3. In that order

Yeah that's basically it. It is a bit complicated to setup but once you have it, it works like a breeze.

Because Jellyfin is plain and simple and does not try to sell me "services" or "content" made by plex. It just plays what is on my drive

I'm thinking of switching to trillium from obsidian too. Most important point for me here is mobile support and note sync. How does trillum web support mobile phones ?

A full setup around managing and download multimedia content

• Jellyfin for playing everywhere
• Sonarr and Radarr for automatically renaming and sorting
• Prowlarr and QBittorrent for downloading
• Filebrowser as a kind of light-weight cloud
• Caddy docker proxy for handling every service a subdomain
• And a bunch of other tools for sysadmin tasks