What about something like this? (assuming SelfServicing TemplateSet):
ImageCollection imagesToSave = new ImageCollection();
try
{
// upload each image and add new image to the collection
forech(string path in imagesToUpload)
{
// build the string path + filename destination
// upload the image
...
ImageEntity image = imagesToSave.AddNew();
image.FilePath = theFinalFilePathDestination;
}
// save the collection
imagesToSave.Save();
}
...