Justin Blanton, in a piece only a veteran-nerd-blogger-type like myself could enjoy all the way through, is dancing on two directions to take his blogging technology. On the one hand, he'd like to stop worrying about the entire stack and just get down to writing. On the other hand, he wants to be up to his ears in control but he'll have to manage every last bit.
The simple solution:
Ideally, I think Squarespace is where I’d like to end up, because it would offer me the most peace of mind. I’d never have to worry about upgrading or maintaining anything.
And, the solution that offers control:
Moreover, to publish a new post I simply create a new file, supply the relevantYAML Front Matter, write the post, save the file, and execute
rake generate. Those commands cause Octopress to re-build (on my personal machine) the site’s pages and upload them to the server.
Every blogger that's been doing this awhile has had a similar struggle. Probably more than once. Before WordPress came along I had my own blogging platform that I built in ASP. Then I had one in PHP. And since switching to WordPress (when it was still called b2) I've dabbled, installed, imported using just about every service/script imaginable - including the two Justin is playing with right now.
As a writer you'll want to play around with new tools. Shake things up and find some sort of writing zen to get back into the groove. But the technology doesn't matter to anyone except the person(s) maintaining the site. If Justin wants a suggestion I'd suggest that rather than switching CMSs to use a different text editor to write his posts. Rather than MarsEdit, use nvAlt (it is what I generally use). Or any of the dozens of good editors for the Mac. It will shake things up for you creatively while not taking up your waking moments worrying about switching.
Blogging is a simple medium - whatever you choose to use is typically good enough. WordPress is now more powerful than it needs to be for blogging. So this can get daunting. But, at the end of the day, we're serving up blog posts. Install WordPress. Install a caching plugin. And that is all you will ever need as a blogger.
Oh, and Justin, you're a huge nerd. We love you.