For me, lack of nice (ie. controllable, but 'automagic') image handling is a huge bug bear in nearly every cms out there, static or otherwise. Perhaps I didn't find the right platform/plugin...
In my case, I wanted to have 1 source image that was resized at various (author controllable) sizes and then saved them, while also generating supporting HTML (eg. 'srcset' to automatically swap between them). I ended up with a couple of ways to template it in [0]:
I think this is a task that is handled by an optional CMS, not the static site generator itself, though I agree it would be handy to have a little helper snippet to do that during build.
There are CMS solutions for static sites which will probably handle images, and all kinds of content, easily. Check out Dato[1], Siteleaf[2] or Netlify CMS[3].
Alternatively you can use external tools to prepare your images and simply rely on the standard HTML srcset within your static site generator of choice. I use RetroBatch[4] to prepare my images.
Exactly what cmroanirgo describes, also see my reply to epage (https://news.ycombinator.com/item?id=17961353) for that and my problems with rss, and some other things I didn't mention. For images, I ended up writing my own metalsmith plugin to resize images to different sizes and add all the attributes to the tags properly.
Are creating RSS templates [1] considered as "handling the complexity", or is that too much hassle?
[1]: https://github.com/atmoz/atmoz-net/blob/master/.ply/feed.tem...