More than a year ago, I have switched my two blogs from Drupal and Wordpress to Jekyll. There are some tools for blogging from the iPad for Drupal, and more and better ones for Wordpress.
What to do if you are using Jekyll to generate static copies of your blog?
What I am doing is writing my posts on iA Writer for iPad, and having it linked to my Dropbox account, I can work on drafts of my posts while resting peacefully in a cafe, or any other place.
I do not have a 3G iPad, just a WiFi one, and of course an external keyboard. If there is no free WiFi available I can tether internet using my old Samsung Galaxy Ace.
I store my drafts in a _drafts folder, or better yet in some other Dropbox folder, not under the Jekyll tree.
Once I'm happy with the draft, I can wait until I'm in front of my Laptop or Desktop and run the
jekyll command. But if I really want to publish the post immediately, I use iSSH to log into my Desktop PC at my office, which is always on, and re-generate the blog, which is automatically published thanks to Site44.
Blogging while not in front of my computer, or even using the iPhone, was something I usually missed about not having a Wordpress/server setup. On the other side, the responsibility to have everything running, apply patches to Linux (I am crazy enough to run my servers on Arch), and to Wordpress, finally tired me.
My actual setup is much easier and lighter.
I can blog from any place, and I can post from almost any place.
If you have some other setups, I would like to know about them.