Yeah I've tried uploading to regular site galleries in addition to my member gallery but neither works. Here's how I think we should break it down.
1) If Flash upload is OFF my account uploads just fine, to any category and any amount of files (1 or multiple)
2) If Flash upload is ON my account fails to upload to any category and any amount of files.
Whatever security checking is done for the FLASH upload must be different from the security checking for the "regular" upload. So what I'm asking is where in the code are those security checks performed for the FLASH upload, it must be some additional file or some additional code that is called for the FLASH uploader that isn't called for the regular upload process. That's what we need to pinpoint to try to isolate what variable or check is failing or isn't what we expect it to be for success.