I'm pretty sure we'll use Jekyll + S3, because:
- Both Jekyll and S3 are incredibly popular right now. This brings many advantages: I will be able to keep them running for a long time, and be able to install them on new computers if need be; incremental improvements will continue for a while; answers are easy to find on the web; etc...
- very few static site generators support multi-directory organization, but fortuitously, Jekyll is one of them
- Octopress is an option as well, because it's usually considered the better nicer version of Jekyll.
- However, Octopress is tailored more towards blogging. While Jekyll is good at blogging too, it's less focused on that. I want a bunch of pages, not a blog.
- Many of the plugins that work with Octopress also work with Jekyll (or have a Jekyll-specific alternative)