So far I’m very happy with it. Everything is very customizable, setup was super simple and fast, and deployment was a snap! I say that with the caveat that some ruby/rails development experience might be necessary. Was Posterous easier than all of this? Sure, but I’m a developer. I should get to know all this stuff since I have never really used it before.
There is a better reason I chose to use this setup over something like Posthaven, Square, Wordpress, etc. I hope in the future there will be a project for me to flex my Octopress/Jekyll muscles. After all learning new (to me) things is always useful.