When comparing Octopress vs Webhook, the Slant community recommends Octopress for most people. In the question“What are the best static site generators?” Octopress is ranked 4th while Webhook is ranked 20th. The most important reason people chose Octopress is:
Octopress is designed to remove all the time-consuming and frustrating tasks you usually have to deal with when using Jekyll. You don't have to write your own HTML templates or do any configuration to get started. The default template also takes care of any basic CSS/JS you need to write to get going.
Specs
Ranked in these QuestionsQuestion Ranking
Pros
Pro Very easy to use
Octopress is designed to remove all the time-consuming and frustrating tasks you usually have to deal with when using Jekyll. You don't have to write your own HTML templates or do any configuration to get started. The default template also takes care of any basic CSS/JS you need to write to get going.
Pro Lots of plugins (from Jekyll + 3rd party)
Another advantage of being based on Jekyll is default access to the extensive plugin system for Jekyll. There are also plugins developed specifically for Octopress.
Pro Based on Jekyll
As Octopress is simply a framework on top of Jekyll, it benefits from being based on one of the most popular site generators available. The primary benefit is that it is backed by git and is built in such a way that the site can be easily re-generated if the content changes.
Pro Uses Markdown for writing
Uses the Markdown syntax for writing blogs.
Pro MIT Open Source
A very flexible license to do whatever you want. Code available on GitHub.
Pro Friendly CMS that clients can use
Webhook has a CMS admin page that can be access on the live site. This lets your clients login and edit the site like a traditional CMS system.
Pro Works with Firebase
Rather than store the data in flat files, Webhook stores your data in Firebase, where it can be accessed similar to JSON from other applications.
Pro Flexible Content Creation
Lets you describe your own content types and their own fields easily from the admin interface.
Cons
Con Not Actively Developed
Last commit is Feb 22, 2016, Social media hasn't been updated. Dead project?
Con Inefficient
Adding a new post, for example, causes the entire blog to be regenerated.
Con Some plugins have hard-coded values
Con Not as flexible as Jekyll
Con Code and data are intertwined
Con Requires registration
Even simple command line tools require registration.