If the photo manager let you compare any set of photos two at a time, you could (with n-choose-2 keypresses) find something close to a total order of the set. Then you'd easily be able to choose the best photos of the whole set, as well as the best ones of each subject/set of duplicates. No machine learning would be required.
Has anyone encountered a tool like this?
Edit: You wouldn't get a stable total order because the pairwise comparisons might not hold transitively, but something like Elo ranking could work here.