It would be great if wp2mm could handle images embedded in post content.
For example, the migrator could download Wordpress media library images referenced in post content to an 'export/images' directory and appropriately tweak each image's 'src' value in the post content to reference its new 'images/*' location.
I'm working on this (but don't let that prevent others from trying to tackle it). I think the convention (possibly a requirement) is that if a post is named 2014-14-01-my-post.html.markdown that its content goes into a directory named 2014-14-01-my-post.
Wordpress often embeds a scaled version of the image, so I'm working on grabbing the full-sized image out of the wp-uploads directory... though this necessitates then having a dependency like middleman-thumbnailer. So my approach might be overly obsessive in preserving the fullsize original images.
Regardless of what I wrote above, we should probably rewrite the image tag to use middleman's file helper so that the asset_hash works properly. Whew!
@bensheldon downloading wp images looks interesting. Have you made any progress on it? I'd like to help, but need a little more information.
@natedavisolds so, I ended up just brute-forcing the files along with an (unpublished) utility gem I put together for reading and writing out markdown+frontmatter files: https://github.com/bensheldon/middleman_writer
Here is my collection of utility scripts: https://gist.github.com/bensheldon/007781c3c3e6f0afa948
Long story short, it wasn't a very clean process (though my blog has had a couple of lives as it was a Drupal website before I converted it to Wordpress before I converted it to Middleman). But it worked after a lot of finagling. So it may be a challenge to automate.