Multiple File Uploads Form / Enhance

I already have developed a form to insert a new article. This form contains text field, description field, multiple select boxes and 5 file fields (Featured, Icon, Thumbnail, Video, Images), 4 only loop once (Featured, Icon, Thumbnail, Video), and the 5th (Images) loops 10 times allowing 10 images to be uploaded to that mysql table/folder. Each file field uploads to a different directory/folder. My problem is that when I select only 2 of the 5 file fields to be uploaded for example: Thumbnail and Images (with 2+ images selected) the second image uploads to the wrong directory, it uploads to it's parent directory one folder up. I have tried debugging it but haven't been able to find anything. If I select 3 or more of the file fields everything uploads fine. I would prefer to do a skype session just to show you a visual of what is going on. I have not experinced anything like this before, but ultimatly comes down to the code.