Hello ukidnme$ -
Unfortunately the error check on our lister page does not currently check the size of your images for compliance with eBay's size requirements - however I have passed your comments regarding this along to our Product Management team in the form of a feature request for such an ability for their consideration and will update this thread should new information regarding this become available.
As we are unrelated to eBay, we have no control over their requirements or the responses from their API. It is required by eBay that any image in a listing have a minimum of 500 pixels on the longest side, so any image that does not meet this requirement will cause a listing to fail to post to eBay.
In order for us to look more specifically into the other issue you mention with listings, we would need to have a look in your account at the listings in question. I suggest that you file a support case from under the Help tab of the site that includes the details of what you have experienced as well as the titles of the listings involved and we'd be happy to look into it further for you.