I've been using Octopress for the last while and it felt good having a nice fast static blog as opposed to heavy-old Wordpress. After time passed however, I noticed I wrote less. Having to grab my laptop and pull up vim to write something, then play around with git or a sometimes having dodgy rsync problems it made the whole process less seamless. Jumping straight onto Wordpress anywhere I felt like(even my phone), has made the ability to write much more present during my day and naturally as a result I'm writing more.
Anyway, I found a nice little project that pushed a folder of Octopress markdown to a Wordpress XML-RPC endpoint here. It was a struggle to find, if you search for anything vaguely related to Octopress and Wordpress you'll get a million tutorials pushing you out of nasty old Wordpress, not back into. The script didn't work out of the box for me so I added a couple of fixes, which the author nicely accepted. Hope it helps!