I recently started using Jellyfin for friday movie nights with me and a few friends who no longer live near each other. The sync feature on the web UI works surprisingly well, we hang out on VC and it's as close to watching something physically together it can be. Overall I've found it to be really solid, although I've not really dabbled much with other media center software to compare it to.
My only real complaint is that for whatever reason it really does not like my folder structure - most of my files work but it'll randomly decide that a bunch of episodes in a folder are a single "file" with multiple "versions". Reading their docs it seems like they really want you to conform to a specific folder structure, but not only would this take me forever (I've been growing this collection for 15+ years now!), I just don't want to change it; I'm happy with my folder layout and it makes sense to me, it's really surprising that Jellyfin can't just show me the raw files.
My only real complaint is that for whatever reason it really does not like my folder structure - most of my files work but it'll randomly decide that a bunch of episodes in a folder are a single "file" with multiple "versions". Reading their docs it seems like they really want you to conform to a specific folder structure, but not only would this take me forever (I've been growing this collection for 15+ years now!), I just don't want to change it; I'm happy with my folder layout and it makes sense to me, it's really surprising that Jellyfin can't just show me the raw files.