gfree_au

I recently had to do something similar for a friend, I wrote a small post on how I converted squarespace to wordpress (with images);

Import Squarespace to WordPress

Hope it helps a little.

I had to do this recently, I wrote a post on how to do it:

How to import posts from cute news into wordpress.

I made a post on how I use post thumbnails with twenty ten, works well for me: http://www.keleko.com/2010/setting-up-post-thumbnails-in-wordpress-3-0-with-twenty-ten/