Isn’t ripping your own media the sort of use case where Plex really shines as a solution and is fairly user friendly?
Also, I think anyone that tells you that you can just have always-online media that you don't have to babysit is lying. As far as I can tell, that doesn't exist. Your server will break at some point, for no apparent reason, and you're going to have to fix it. Usually the fixes are easy on their own, but you end up accidentally nuking the RAID and losing all your rips. It's hardly "user friendly".
This isn't crapping on Plex, it's sort of the nature of the beast
That’s certainly more than many people are able (or willing) to put up with, and it requires a several hundred dollar investment. But NAS ease of use for common tasks is pretty good theee days.
Dude, really bad example, printers are hell to set up.
I think 99% of problems are wifi related or trying to share the USB connected printer over the network.
I've had jellyfin serving my music, family videos and youtube rips (e.g. university lectures) for years. Haven't had to touch it since I set it up. I just plop files into folders and it picks them up.
I got a lot of family videos from my mom, who keeps them on her computer plus an external hard drive, which she brought to me to copy. Copying files to USB drives as a backup and sharing that is pretty understandable for non tech people.