Wordpress Post Submit Form with Multiimage Upload

I am working on a smaller project and am attaching 2 files that make up a post form that I am using to allow post to be added to Wordpress without people having to go into the admin. I have it working and able to be used with or without authentication based on settings in the theme I am using but i really am stuck on getting the part where images can be uploaded. I have the custom fields and wordpress post fields saving but gave up on images. I would like to go with multiple images... eventually where the number allowed is set from my theme. You will see in the post form that I have 5 individual file browsers which I guess is one way of handling but rather static and not flexible. I guess in a perfect world having a image uploaded that would allow multi uploads like WP flash one does or like Gmail attachments do would be great but not sure what is best for this kins of form.