Every single time I talk to my friends, whom also want an *arr/Plex/VPN/Home Assistant setup like I’ve got, I can see the fear in their eyes when I mention Debian, Docker, and the terminal. It could be a case of “git gud”, but I want to help them out with a setup like this, but with as low friction as possible. Ideally something completely GUI based, and very low maintenance.
I know of unRAID, and Portainer, but does anyone have any experience in setting up something like this for people whose knowledge of self hosting and networking aren’t as good as yours?
I know this is not the answer you are looking for, but if they happen to have a spare Windoze license laying around (or willing to shell out) then all that stuff can be done on an OS they are probably comfortable with. Yes, it still means learning some stuff, but there is no overwhelming need to learn an entire OS to do it.
Another option is to use a Synology NAS. All those things you are talking about are packages, point and click install and setup from the NAS browser. Again pricey, but far more intuitive for non-techos. This also has an advantage of being able to upgrade as their media store gets larger.
(I don’t do either of these things, but I know we support a lot of people radarr/sonarr/lidarr/nzbget/plex/emby/HA/openHAB etc in a win environ.)
But I would teach them how to git gud, and learn FOSS and read HOWTO’s to install all that stuff (without the need for Docker, so they actually learn). Honestly after the first 5 installs on a VM (which can be deleted and recreated if fscked up) running
sudo apt update && sudo apt upgradeand git clone … etc. with you looking over their shoulder while reading the HOWTO with them. That would be quite rewarding for them, probably make you feel good too.