The real problem with any SSG is where to host and edit Markdown files and images for flexible spur of the moment content creation. I've built my own Wordpress-export-to-static solution to use the native iOS App as a workaround but it feels somewhat clunky — Same with having to run a headless CMS for this in the background; Surprisingly with all the gazillion of MD editors, no one has ever built one with live editing…
In my opinion the best solution is to find some sort of happy medium. Static site generators are excellent in terms of weight and speed but a lightweight file based CMS can be almost as fast while still providing the needed flexibility.
My site currently runs on Kirby (https://getkirby.com) but I write almost everything on iA both on my Mac while I'm at home and on my phone while I'm outside.
Updating the site is not as simple as typing a command on a terminal but it's just a few clicks on a very simple and minimal UI.
Images are hosted on my server like the rest of the content. It's a simply DO snippet with no fancy configuration.
If you want to go down a more automated solution, iA comes with support for micropub so you could in theory set it up so that you can upload a new post without leaving the iA interface.
But imo it's a lot of extra backend setup that needs to be monitored to save very little time in the long run so for me it's personally not worth it.