> And I just keep getting bitten: someone else's tool gets so big and moves so rapidly, that by the time I get around to updating my site, []something about the new version of the tool has broken the way my web site works. And then I usually have to spend hours figuring out how to fix it[], which is hugely deflating because I had just worked up the energy to write a new post. My naive belief is that if I have my own tool that evolves at precisely the pace I want it to, I won't run into that specific problem. I'll run into other problems of course, but I'm thinking that I'll prefer those problems to the ones I currently face.

This is true, as a general principle, not just of static site generators, but of all software, and is one of the major Reasons Why We Can't Have Nice Things, and why automatic updates are evil and poisonous, and manual updates dangerous and often-avoided. See eg https://jacquesmattheij.com/why-johnny-wont-upgrade/.