Fellow raw HTML writer chiming in. My hand-built little web app for blogging broke maybe five years ago with some OS X update, and I have been too lazy to fix it.
Also a raw HTML writer, but I’ve been considering the SSG route to make site updates (global nav changes, redesigns, etc.) manageable. You seem to have some method of handling this on your site, given that I can view a page of posts from 10 years ago and still see links to this year’s posts. How are you doing that with raw HTML? (If this question doesn’t make it clear, I am quite amateur.)
I had a PHP script that did this for a while — I would write the post itself by hand, then put it into a database; the PHP script would regenerate the site locally and take care of things like nav links; then I would rsync the static output to the web server. Once I figure out how to get it all running on the latest OS X again I'll use it again; I'm a big fan of this kind of setup. I'm sorry that I don't have specific tools to recommend for it.
