> I'm talking about managing two certificates so I can share a static site with a handful of friends. Each one takes about 10 minutes a year to update.
The personal site I started with is one certificate for a static site that I use for basically the same thing. It took me 10 minutes to set up in 2016 and I haven't thought about it for a second since then. It just works.
> Adding automation means I have to set up a process that I have to check up on at least once every 6.5 weeks to make sure it's still working.
Assuming you're using a common automation package and not rolling your own it should be included. I personally use acme.sh which can be configured to use email, XMPP, or HTTP(S) requests with prebuilt templates for most popular webhooks, as well as supporting fully custom notification scripts. I get an email every time it attempts a renewal that tells me if it succeeded or failed. Again one-time setup, easy, did it once literally almost a decade ago and haven't had to think about it since. As I pointed out in my previous post I did once have two of my systems fail to renew, I was notified, and I fixed it within a few minutes of seeing the emails.
Now that I'm actually thinking about the topic, these days for my work systems I have a platform that monitors for periodic updates and alerts me if they don't come in so I should probably reconfigure my notifications to use that instead of email and clean up my team's inboxes a bit by no longer needing to receive a couple dozen "everything's OK" mails every couple of months (or soon, couple of weeks).
Adding automation means I have to set up a process that I have to check up on at least once every 6.5 weeks to make sure it's still working.