I wrote a plugin to let me organise assets in subdirectories easily:
https://github.com/samrayner/jekyll-asset-path-plugin
{% asset_path my-image.png %}
in post 2013-01-01-post-title would output:
/assets/posts/post-title/my-image.png
in page my-first-page would output:
/assets/my-first-page/my-image.png