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Movies
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https://support.plex.tv/articles/local-files-for-trailers-and-extras/
Short answer is put a tag like "-featurette" in the filename, or add a folder to contain the extras.
Jellyfin supports the same structure as far as I can tell. One thing I've found Jellyfin does better is in allowing you to organize extras for TV shows in with each season, while Plex only seems to allow you to dump all the extras into the root folder for the show.
I was hoping someone with experience with Jellyfin would reply here :D. Plex has worked well enough for my needs for a long time, but I keep seeing praise for Jellyfin here on Lemmy and I'm always interested in free and/or open-source alternatives. I've only got a handful of DVDs left to rip, and once I'm done with that I'll be looking into Jellyfin!
I've got both Plex and Jellyfin running at the moment. Plex is nice for sharing with family since it's more plug&play for sharing outside your LAN, and it is certainly a little more polished in some areas.
But I've been very impressed with Jellyfin as well, and would wholeheartedly recommend giving it a whirl. If FOSS appeals to you at all, it's a solid choice.
In most cases, you really should have no issue running them simultaneously if you're not ready to commit to a switch.