One thing I can see that Webby supports that looks interesting is ERB. How flexible is ERB as opposed to what seems like a more restricted templating language like Liquid? It looks like ERB allows for actual Ruby to be used in your templates which would have ultimately solved the issues I had.

ERB is simply embedded ruby, it has no limitations. It is also totally not secure when used on a server.

My guess security of GitHub Pages is the reason for using Liquid in Jekyll. For generating static pages on your desktop before uploading Liquid is simply not needed.

I am a bit surprised jekyll is so heavily promoted as a static site tool(saw it twice on HN front page already) while an elegant and seemingly more powerful ruby application (webby) already exists for this purpose.

From what I have just read about Webby, it seems like it does not support topics and categories like Jekyll does. However it does have a wide range of rake tasks which do some things like offer a variety of deployment options, logging to growl, and validating links.

There are differences in the philosophies behind the 2 projects. They are both static site generators however Jekyll is more oriented for maintaining blog-style sites. Webby lacks the ability to organise content the way that Jekyll does.

Perhaps most importantly, Jekyll is now available as a free, hosted solution with GitHub - a great way of inviting the large community of developers active in that community to contribute to the project.

I am not saying one is better than the other. They seem to accomplish slightly different things although the method in which they go about it is somewhat similar.

Sadly, you have not read enough before making your conclusions. Webby shines with blogs, check http://www.locomotivation.com to see an example.

You can create a blog with two commands in webby:

   $ webby-gen blog "My Blog"
   ...
   $ webby blog:post "Nice weather today"
   [13:27:47]  INFO: creating content/blog/2008/index.txt
   [13:27:47]  INFO: creating content/blog/2008/12/index.txt
   [13:27:47]  INFO: creating content/blog/2008/12/28/nice-weather-today.txt

And it obviously does support categories/tags/article statuses etc. since you can give any property to your page.

Well if that's the case and if properties are available on a site-wide basis like Jekyll's topics and categories are, then yes - it certainly seems very capable and something I would like to have a crack at using.

Yeah, Webby totally kicks ass! There's no point of re-inventing the wheel, especially when the "current" wheel is so nice...

And since everybody thinks the GitHub guys are cool, lots of people are going extend Jekyll with all kinds of features that Webby already got.

Consider Webby and Jekyll as descendents of a common ancestor idea. They share many things in common but are adapting to different needs. Most importantly, because Jekyll is restricted to Liquid for scriptability, it is safe to run server-side. Jekyll also processes non-Jekyll (plain HTML) sites unchanged, whereas Webby refuses to run at all without a config file. Jekyll also relies more heavily on conventions to reduce the organizational overhead of the maintainer. Webby is a great system, and I'd like to pull over some features from it, but I will do so under the philosophy and adaptations of Jekyll. Besides, if you like how Webby works, then you can use it to generate a site and push that to GitHub, just like Webby intends for you to do!