I found an interesting new program yesterday. It is zpu (ZenPhoto Uploader). It is exactly what I was looking for. It allows you to upload entire directories of photos without having to do it manually with the webform. I know it can be down by ftp but I am using an easy one click install from dreamhost for simplicity and it only supports the web form upload process.
So zpu saved the day for me. I had to make a few changes to make it work on Windows; they have since been included to become 0.2.