I added https to my static site last year and it has been a huge waste of time.
ubuntu + nginx worked fine for years without much maintenance, but I've spent so much time reconfiguring things when something breaks (and it is really clear when something a renewal fails... thanks HSTS).
Things that used to be simple, like putting setting up a subdomain (need to get a new cert and reconfigure the cron job now) or pointing at a websocket (can't point directly at node since that's not secure, needs to pass through nginx now) consistently take hours to do now.
I mostly do data analysis and front end work; mucking around in nginx config files is something I would have been happy never experiencing. It sucks that it's harder to host your own website now.