I don't use Turbo Lister but I have used File Exchange to upload some listings. I have seen similar behaviour using that tool.
If I upload my pictures to an external server first then use a pic URL in the images field then multiple pictures (including variation pics) will be on the listing when the job is done, but hosted on the remote servers. ie self-hosted.
But... but... and here is the cruncher... if in the future I go to manually revise that same listing all but one (the primary image) of the images will be removed from the listing. Just disappear as you say!
The only way to get them back is to manually add the pics back onto the EPS.
The problem with doing this is that ebay will not allow you to have mixed image sources on the one listing. ie some from self-hosted and some from EPS. Most of our products have variations so we have variation pics loaded as well. So to correct the listing you have to remove ALL images (incl variations) first then manually re-upload them all. After painstakingly doing this all the pics then reside on the EPS and the listing behaves as it should. Future revisions work ok after that.
So... I have stopped using File Exchange to upload new listings. Its useless this way to me. I called ebay technical team about the problem and all they would say was that they were aware of the problem and it was on the table to be fixed up but would not commit to a time-frame. I wanted them to include an option in the File Exchange upload so you could choose whether your images reside on EPS or be self-hosted. Simple solution to me. Unless you have an exceptionally fast external host server, keep in mind that EPS will always be faster to display your pics to a buyer. Slow image loads might be a bit frustrating for a potential buyer.
So these problems you describe for TL could be related somehow.
