Okay so I broke down and thought I'd try another way to upload images from my iPad to Wordpress. Here's what I did, I'm not even sure this is going to work the way I wanted it to. I purchased the FTP On the Go app from the iTunes Appstore. Configured it for my FTP server, grabbed an images, navigated to my image gallery, I'm using the nextgen gallery, so it will be located under your wp-content/gallery directory. You may need to drill a little deeper to find your directory but I think you get the idea. If this actually works I will clean up this post with pictures and what not. But for now I will just add the picture that I "successfully" uploaded.
Until next time,