I converted my site to static HTML about two years ago, using Octopress. It was a combination of getting sick of Wordpress breaking, and being able to handle hu

I converted my site to static HTML about two years ago, using Octopress. It was a combination of getting sick of Wordpress breaking, and being able to handle huge traffic rushes. (My first time hitting the front page of HN, it crashed my site a couple times with WP). Here's the thing though. You're trading one headache for another. Ruby is a fast moving, but fragile ecosystem. Octopress (which uses Jekyll) is easy to set up, and easy to customize. But long term... it's a PITA. 1. If you want to develop your site on more than one machine, you'll find yourself installing a bunch of bundles, then porting over your source files and finding it doesn't work. This has happened several times. 2. If you want to go cross platform - good luck with that as well. If you want to generate your site on Linux it's super easy. OSX or Windows - a small nightmare most of the time. I haven't really figured out why this is. 3. If you try to pull down the most recent version of Octopress or Jekyll and merge it... yeah you're going to break stuff a lot. Get ready to install a bunch of gems, and roll back versions of stuff sometimes. 4. Get ready for some random breaking. It happens, especially if you're updating packages. Jekyll will just break. 5. Every time you Google something, you usually find a bunch of Jekyll users asking the exact same question as you, and many times it just leads to a bug report on the Jekyll GitHub page. All in all I would say it's still less hassle and bloat than WordPress, but you really do trade one annoyance for another. Because static HTML is so much faster I decide to stick with these hassles. Jekyll is fairly good, but Ruby is an unstable ecosystem for real work. I think Jekyll would be a lot better if it were pure Python, or something similar.