I think your approach is great.  There&#x27;s clearly a demand for simple static site generators that favor configuration over convention, so unless you <i>really</i> want to pursue the Middleman audience, I&#x27;d keep on keeping on.  But I&#x27;ll offer a few thoughts for your purposes:<p>1.  I think a small, well-tested core like you&#x27;re doing is great.  I also think for your purposes, Mako templates are the right way to go, since they allow super flexible logic in the templates.<p>2.  If you want some inspiration from a kinda sorta similar approach, take a look at Metalsmith and its plugin ecosystem if you haven&#x27;t already.<p>3. A great asset to any static site generator would be a collection of &quot;starter themes&#x2F;sites&quot; that already have things like a static asset pipeline set up (using Gulp, Grunt, or whatever floats your boat).<p>If you <i>really</i> want to accommodate the bigger static sites, a few critical features:<p>1.  Super fast compile times.  This is why Hugo is rapidly gaining ground despite not having a plugin API. When you have thousands of static files, it&#x27;s not fun waiting 10 or 20 minutes for each compile (Middleman and Jekyll have gotten faster, but they&#x27;re still slow relative to Hugo and the Node-based static site generators).<p>2.  With huge sites that are built by large teams, flexible templates like Mako almost become a liability, since careless team members can overload logic into templates.  For these teams, you may wish to offer an alternate template choice, like Jinja.<p>3.  Some kind of feature similar to Middleman&#x27;s dynamic proxy pages, which would allow users to dynamically generate hundreds of pages basic of Contentful&#x27;s API or their own JSON files.  See: <a href="https:&#x2F;&#x2F;middlemanapp.com&#x2F;advanced&#x2F;dynamic_pages&#x2F;" rel="nofollow">https:&#x2F;&#x2F;middlemanapp.com&#x2F;advanced&#x2F;dynamic_pages&#x2F;</a><p>Finally, features Middleman&#x27;s url helpers have proved to be a significant help on large static sites I&#x27;ve worked on, since the URLs are no longer hard-coded.  There are a lot of small but significant features like this: localization extensions, pagination, etc.  But if you have a good plugin API, all of these things can be created and offered as plugins.<p>But again, I think your current approach is just fine.  If I were you, I&#x27;d perfect a simple core generator and then try to build up the ecosystem.