2.) Each of our products have over 100 images, we have over 100 products. So you are confirming that I must select EVERY box, individually, for over 100 images, for over 100 products, in order to translate the Media? This is 100% asinine.
Unfortunately that's how it is for now. I discussed the matter with my team and we understand that when there are so many images (like in your case), the task becomes time consuming. I'll create a feature request for this issue, by splitting it into a separate ticket. So we can keep track of it accordingly.
Just wanted to update you that this should have been fixed in new version 4.7, where now all relevant images for the posts are included when the post is selected for translation from TM Dashboard.