I don't keep track of them. Jellyfin and Radarr, etc. keep track of them for me.
Yeah Radarr and Sonarr for me. Does a really good job at it too. Haven't tried Jellyfin myself.
Jellyfin combined with Radarr and Sonarr is freaking amazing. Add in Jellyseerr and you've got yourself a Netflix competitor in your own home.
I actually had to look up what Jellyfin was prior to commenting again. I use Plex to stream to my devices. They seem pretty similar from what I can tell.
They are pretty similar. Plex is more polished though. But what keeps me from using Plex is that the client likes to push content onto me that isn’t on my server. I can unpin those suggestions, but they always came back after some time, which annoyed me. I also don’t like how they handle account authorization. I shouldn’t have to use their servers to log into my own server.
Jellyfin doesn’t phone home ever, and it only ever shows my content.
All that being said, if none of that bothers you, Plex is still a really good media server.
What kind of files?
I use Kodi to keep track of what TV shows and movies I've watched.
Mine just go in folders: Movies, TV Shows, Education, etc
You are going to have to be more specific about the type of files if you want useful advice.
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