markdown2wp.com is comprised of two python scripts for posting entries written in markdown syntax to a wordpress-dot-com blog, and for uploading images for the post. Right now, the imageupload doesn't work very well. But, this is public domain software that carries no guarantees. I'd still probably suggest leaving the image uploading out until I can get it to work a little better.
Python 2.6.x or higher.
There are a number of dependencies not in the standard library that are necessary:
keyring
markdown
yaml
kitchen
Image uploading also requires BeautifulSoup.
I'll leave it to you to install those with pip or easy_install.
For more information on using this script, see this post on my blog!