I'm actually coming up on ten years of having the same blog: waaaayyyyy back when I started, I was editing all my pages manually. (Though blog posts didn’t have permalinks, it was just a growing massive "list page" that I’d break off and paginate every so often.) It started to become a pain in situations where I wanted to modify some basic aspect of every page: I’ve consistently gotten the itch to either re-architect or re-design my blog annually.

You really can’t beat a system that uses templates.

I'd tried my own Javascript-based content system in the past (where everything is based on one HTML page and JS loads the page content), but those add a bit more client-side complexity (not to mention search engine reachability).

I think the ability to regenerate an entire 500+ page static HTML site is pretty powerful and useful. (Also: who wants to manually update date-based URL paths every time there’s a new thing? http://v3.mike.tig.as/blog/2012/06/30/ http://v3.mike.tig.as/blog/2012/06/ http://v3.mike.tig.as/blog/2012/ etc.)

EDIT: As to your first question wrt "dynamic features I wanted": CMS and full control over my site's behavior and templates. It’s Django-based, too, so I can theoretically extend it with any features as necessary. (I also have plenty of "non-published" content that I can view on the local, "hot type" development server of my site, but the "renderer" file is only configured to upload blog posts marked as "live". I find that feature pretty useful.)