I haven't taken the time to learn ajax at all but I've seen what its capable of so I was assuming it was possible.
Okay moving past the drag and drop also.... How about simply one file browser and allowing for multiple selections. Press OK and it adds to the upload list. You hit Browse and you can select even more in case you need to add from multiple folders on your computer. Then hit Upload and it uploads them.
--------------- Added [DATE]1200768717[/DATE] at [TIME]1200768717[/TIME] ---------------
Check this out:
http://digitarald.de/project/fancyupload/
Click the demo, it's absolutely perfect.
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I just need someone that is savvy enough to integrate that with VB.