I've been using it for about 4 years now, and I simply haven't had the time to convert it to anything else but plan to as soon as I can.

Over the last couple years I've dealt with countless type error issues, gem incompatibilities, etc. I have one single machine that Octopress generates my site from now, and it's an old Linux install that I refuse to update (because that will break OP). I believe the author tried his best to make what's essentially a clever Jekyll hack work as well as he could. He's tried creating a newer, smarter version but I'm not sure what the current status is. I'm guessing it's going slowly because most he, like most people, don't have time for such a huge project that isn't paying bills. I appreciate the attempt for sure, it worked great at first.

I don't want to sit and complain about a free product but would caution others about investing in it heavily like I did. I spent a considerable amount of time on overhead with this product as it sits. There are much easier (non Ruby!) solutions out there.