I am having the same problem. It appears that if you do not include an image with the original listing there is now many to manually "push" the system into adding one later. I had updated the ebay listings with the corrections. How do I ask tech support to updated the gallery?
http://cgi.ebay.com/ws/eBayISAPI.dll?ViewItem&rd=1&item...=STRK:MESE:IT&ih=004