That’s very close to what I’ve been doing. I’ve been using the suggestion about shortcodes from this post and like you said putting the images in the static folder. Then in the code I write:
<img src="{{<baseurl>}}/images/.../myImage.jpg">
This then makes the images safe to load from both the main index page and the single page. I just wish I could use the bundling feature so that I can keep the images along with the posts but it’s not possible. To keep things sane I’m mirroring the directory structure of the posts under the static folder.