Automated payments are a different matter from automated infrastructure that's already been paid for.

I have automated tickets created when I need to do things that I haven't automated yet, but, I still want to automate as much as possible.

I have not run into the problems that you're suggesting I should've. If a server no longer works or was confiscated, why would I still have DNS pointing at it? And does it really matter if I have some servers renewing certificates unnecessarily anyway?