If you can't keep your site's certs working, I don't have much faith you can keep your server working. Maintenance is required in the face of entropy
EDIT: I have 15 year old things at work that do not compile, you have to maintain it for sure, biggest problem is cryptography. I am not sure that unstable tech should be part of the application ever.
If we're talking applications that don't actively listen on the internet that's fine, and I would agree that we should have complete software that just works. But a webserver, unless it's for personal/home use, it's on the internet and I don't see how it could work for 35 years without any update/change