I don't think this is "contempt for users," it's a position that configurations that appear to setup a web server to run without monitoring for years are decept

I don't think this is "contempt for users," it's a position that configurations that appear to setup a web server to run without monitoring for years are deceptive and harmful to the admin taken in by them. It's an ethical (and technical) position that tools should push their users to adopt maintenance practices that are seen as responsible by the wider community. It's not contempt to inform people about the level of work you expect is required to do what they are planning. It's also, if letsencrypt happens to be wrong, not contemptuous to be wrong!