He did say "easy to manage". I guess that's relative. Having the database always available has some conveniences (e.g. you can actually have comments on your pages instead of a JavaScript placeholder), and using a platform that's both really popular and quite mature has even more. A couple of comparisons should illustrate:
How to write a post with WordPress:
1. Click the + button
2. Write
3. Check the tags you want
4. Click publish
How to write a post with Octopress:
1. Type `rake new_post["whatever you want your title to be"]`
2. Navigate to source/posts/yyyy-mm-dd-whatever-you-want-your-title-to-be and open it
3. Type your post
4. Enter the categories in brackets at the appropriate place in the YAML front matter
5. Go back to the root of your site and type `rake generate`
6. Type `rsync -az public/ user@yourserver.com:yoursitedirectory`.
This is based on the Octopress documentation -- I've only ever used naked Jekyll, but it sounds fairly similar, so I don't think I'm being too unfair here. I'm also giving Octopress a lot of leeway by e.g. including the press of "publish" as a separate step for Wordpress but not the equivalent step of saving when writing for Octopress.
It only gets harder from there. Installing and tweaking a Wordpress theme or plugin is pretty easy. With Octopress, you actually have to sit down and code.
I get that some hackers might be into all that, but surely you can see why somebody might find Wordpress more convenient.
[0] http://octopress.org/