I bought both Plex and Emby. I started with Plex but had some technical issues related to my machine having multiple IP addresses so I switched to Emby. I tried Jellyfin before switching to Emby but it wasn’t as capable as Plex or Emby (at least at the time) and I wanted something with some commercial support behind it. I have been pretty satisfied with Emby, but do wish it would get requested features added in a much more timely manner.
I back up everything. I use Stablebit Drivepool with duplication for all of my source code, media, photos, documents, music, books, laptop backups, etc. I back that up periodically to a Drobo DAS and 8 Bay USB enclosure setup under Drivepool. I also have off site backup (working on a new NAS which will be accessed over a VPN). I don’t want to spend the time worrying about loosing anything I have put time and effort into. Been there and done that. Drives are relatively inexpensive but can fail without warning.