I recently switched my blog from Wordpress to Octopress. Below are some thoughts/points
I collected during this process.

Summary

I generally like Octopress, and for me there are big advantages to using a static site generator over Wordpress (better security, no mysql, faster).
However there are some issues (mostly minor) that came about as I began to really use it.

The Technology Stack

Octopress is a “framework” in the sense that it combines various technologies into a static site generator. On the plus side, you can leverage
lots of interesting tools. On the bad side, if you are not already familiar with these tools you will have a lot to learn.

You could just use the stock design and feature set, but I think the most common use of this product will to be to customize the
HTML/CSS/JS and stick with the Jekyll page generation framework.

That being said, to create a custom theme you will need to understand the CSS/JS/HTML (unless you start from scratch) along with the SASS & COMPASS
technologies.

If you run into any bugs or display issues there are a lot of layers you may need to pull back. The below list is what I consider
the significant technologies in use. If there is a display error (for example an IE8 bug I found) you may need to go through a lot of layers in the
stack before finding the cause.

Source Control, Configuration, Preview, Build, and Deploy

  1. Git
  2. Ruby
  3. RVM
  4. Rake
  5. Jekyll

Theming (CSS)

  1. SASS
  2. COMPASS-style

Theming (JS)

  1. Modernizer.js (including plugins like respond.js, yepnope.js)
  2. ender.js

Theming (Templates & Posts/Pages)

  1. HTML5
  2. YAML
  3. Markdown

Keeping Updated

Updating Octopress from github is not as smooth as it can/should be. My workflo has been to update into a branch and confirm I have a good read
on everything before doing a merge.

This should be improved/less risky in future versions and I already see some tweaks being pushed to github. However it pays to be careful.

Conclusion

Octopress is pretty cool and if you have the time to tinker it can be a lot of fun. I would just re-iterate that it’s still relatively young and is a work-in-progress.