Similarly: I have a static site (no tracking, no PIIs) that's currently hosted on a friend's VPS. HTTPS is out, because they're already using it for something else, and Apache can't know which vhost the user is requesting in time to present appropriate certificate. Maybe there's a workaround for that, but neither I nor my friend know of any, we've both already spent few hours looking, and I do not feel like spending even more time figuring out, or moving it to a dedicated VPS with its own IP.

Basically, on the one hand I'm all happy. On the other hand, I totally do not want to do the work.

And beyond that, all the extra complexity introduced everywhere that you mention, and that I also had happen to me.