That's the problem with Static Site Generators (SSG) in general. They're opinionated by nature and the learning curve could prove steep to process all the details of the configurations necessary to get the maximum mileage out of the framework but as you dig deeper and deeper, you realize that you'd be better off building your own framework that's fit to your objectives and use cases and improve and expand on that as you go along.
I disagree. The great thing about SSGs like Jekyll and Middleman is that they're very easy to build plugins for. Jekyll in particular is easy to learn, and easy to expand. I honestly can't imagine a bona fide programmer having that much difficulty picking up Jekyll.
If you did want to build a custom SSG, I think you're best bet is starting from Gulp, and building from there. At least then you can leverage the Gulp ecosystem instead of re-building everything yourself.
I'm building my own productivity software program using Rails for this reason. I want to see only what I want to see on that page, I want nobody else's ideas getting in the way. It has an intended audience of exactly one, and will in all likelihood never acquire another user.
