Wow, this program, Hyperimage, might do it in one fell swoop; grab all the images from a website and download them onto your hard drive. However, the one bad thing is that it still would not be easy to pick and choose them to reinsert them into the proper posts here at WordPress. While it saves time on the one end, on the other, as I pull them off individually I rename them to the post date and category so I’m sure they’re going into the right spots, and they’re filed in a year/month (if necessary) manner. However, if it retained Typepad’s file path structure intact, it might be a case of just taking off the .html and uploading them to WP.
Might be worth a try on the demo.
The Lost Children: A Charity Anthology