What is your setup? I have TrueNAS and there I use the apps that are easy to install (and the catalog is not small) and maintain. Basically from time to time I just come and update (one button click). I have networking separate and I had issues with Tailscale for some time, but there I had only 4 services in total, all docker containers and all except the Tailscale straight forward and easy to update. Now I even moved those. One as a custom app to TrueNAS and the rest to proxmox LXC - and that solved my tailscale issue as well. And I am having a good time. But my rule of thumb - before I install anything I ask myself if I REALLY need this, because otherwise I would end up with like a jillion services that are cool, but not really that useful or practical.
I think what I would recommend to you, find platform like TrueNAS, where lots of things is prepared for you and don't bother too much with the custom stuff if you don't enjoy. Also I can recommend having a test rig or VM so that you can always try first, if its easy to install and stable to use. There were occasions when I was trying stuff and it was just bothersome, I had to hack stuff and I was glad in the end I didn't "pollute" my main server with it.