The article does not talk about numbers. It is hard to understand competition in the field he is applying to. Then having the opinions of his parents does not help, it’s odd I need his mom telling me the CV looks good. It would have been better to question Princeton here as it is in their interest to make sure alumni get the jobs. It would be useful to ask some recruiters about the possible red flags for this guy, just to be sure. In any case sure I understand and sympathise, anyone would be mentally broken after that many job applications.