ML Algorithm for picking the best picture

nah, that just sounds like he wants to get training data from humans by presenting two choices and making the human choose, and then training the model on that.

or maybe it’s some kind of retrieval task where he expects the “10000” pictures to be indexed by feature vector, and the network discovers a user’s preference function by considering which one of a pair of images the user prefers.

in any case, this has NOTHING to do with OpenCV.