I'd totally hijaack the wordpress file uploader (flash version). it's open source and there is php and javascript (ajax) code that works.
shoehorning that nifty interface in would make image uploading a snap for single or multiple..
matter of fact, i intend to do that on a 'guinea pig' board at some point..
Please let me know when this (ahum) plugin
is ready for us to download
.