Hi, I have had that problem a couple of times, but rarely..what I did was upload the pictures first through the images tab on the main page then when making the listing I just selected them from my image bank and they went right in.
Its been my experience that all programs are going to function differently for different users because of the many factors involved in different machines and the programs and hardware already installed on them. For example: ebay does not load up the same on my machine as it does for my wifes machine..the fonts and other things are slightly different and even though we both have a 800x600 screen resolution and have the same default font being used click boxes and other items do not load the same.
Come to think of it there really isnt much that loads the same on her machine as does mine. She has Win2000Pro and I have WinXP Home. I also dont have near as many problems with the 2000 pro as I do XP either. In my personal opinion Windows 2000 Pro is the smoothest running , most efficient operating system I have ever used... I think Microsoft shoulda quite while they were ahead..lolol.