I can only access my services through VPN (tailscale) when I am outside, so I don’t worry that much about security vulnerabilities. And in my experience so far, security updates are usually more stable than feature updates so I install those without hesitation when I have the time.

I try to minimize the maintenance cost (time and energy) by keeping in mind that I don’t have to update or migrate to something new if everything is working as I want it to be. And if I really have to update, I make sure I also have time for any consequences. I also believe the key to a low maintenance server is automation and templates as this makes rolling back to a last known good configuration easy most of the time.

I have also accepted that time and mental energy has always been the price of self hosting. If you lack these things, you would feel like its a chore. If you have plenty, it can be exciting.