Do you have external users (outside your network)? My understanding (and the last time I tried) is that Jellyfin lacks in this department quite a bit. That and ubiquitous clients.
Plex client is available almost everywhere and overall, Plex mostly "just works". The latest Apple TV client changes have me hot and there are things I don't love but that's what's kept me in the Plex ecosystem. I am looking around now though since I'm so disappointed with the new clients/UI.
I have, after setting things up this year. Any user problems were always due to server-side or bad media files. Or on networking on the server side.
As far as I understand it Jellyfin has been improving client availability and to me seems to work well for friends.
I have my friends and family using tailscale + jellyfin. Their only complaint is not having an easy way to watch on Xboxes. I convinced a few of them to plug old laptops into their TVs which is working fine.