I can't see how learning to use a static site generator could be difficult. Wouldn't people mostly just be editing the content and re-generating the pages, etc?
Sure, but what exactly is there to know about it? :) -How to get it to generate a static site from a content directory?
You shouldn't search only for people who already know the static site generator you plan to use: any good developer that uses the CLI will have no problem using it.