I've recently changed things over to use Ghost. Octopress is great, don't get me wrong, but setting up the environment really wore on me and I started longing for a platform that would let me write and publish from anywhere. There are definitely advantages to having a static blog, but I found that it gets in the way of the writing and writing is the most important part of the site.
Transitioning over was fairly easy. I didn't have that many posts, so for the most part, I just copied and pasted them into Ghost and then changed the dates on them. Other than that, the only thing I had to set up for Ghost was a nginx proxy.
That said, I am really excited to see what Brandon Mathis releases in Octopress 3. He seems to really have an idea of where he wants to take Octopress and a lot of the problems with it. I like what I've heard so far, it's just not quite what I'm looking for in a publishing system anymore.