Considering a move from WordPress to a database-free static site using Jekyll/Octopress? Here are some of the important things you need to make sure are there.

WordPress to Jekyll Checklist.md

Static site generators under consideration:

• Jekyll with Octopress (mostly going with this!)
• Pelican
• Docpad

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WordPress vs Static Site

++ YES / -- NO RELIABLE WAY

++ Pagination

++ Multiple Authors

++ Search: Google Custom Search

++ Comments: Disqus, LiveFyre, Facebook Comments

++ RSS Feeds

++ Sitemaps

++ Shortcode Embeds

++ Contact Form: Wufoo, Google Forms

++ Categories

++ Tags (jekyll-tagging)

-- Image Galleries

-- Ping (search engines, content hubs, etc.)

-- Build times^#1

Notes:

• Since each page itself is a static file, you need to look for a proper cache invalidation technique (e.g. last-modified), or your changes won't be visible to the end user who has already visited the page once (and sees the same page).

• You can easily deploy site to Google Cloud Storage via command-line using gsutil.

• Make HTML files for regular pages and 404/500

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#1: On the latest Macs it's like 2 minutes for a well-optimized blog with ~900 posts (i.e. no related posts, sidebar extras, previous & next post links, less archive pages & feeds, etc). If not done right, it can go over 30-45 minutes. And of course, it can be faster if done on a server.