Another thought about something that may give rise to a sense of entitlement, or at least an unrealistic assessment of chances (aside from participation trophies): Indirect effects of yield management.
It is sometimes thought that high yields are desirable to raise a college’s US News rankings. They do that (to some extent), but I don’t think that is actually the main reason why high yields are desirable to colleges.
All of the CC single-digit schools do rather strikingly well in hitting their enrollment targets year after year, without going too deep into the waitlist pool. How can they do this, when students are applying to about 6 to 12 colleges, and the individual decisions are unpredictable?
I think the colleges most likely have fairly sophisticated algorithms to predict the likely yield within each category of applicant (I don’t mean demographics, mainly–more like high school profile, intended major, distance of home from the college, etc.). At any rate, that is what I would do if I had to arrange for (say) 1500 +/- 20 enrollees each year. Of course, they can correct for overenrollment or under-enrollement in the subsequent years, and they do have the overall patterns of yield to go by. The law of large numbers helps. Still . . .
Students who are likely to be admitted to multiple “top” schools create the greatest uncertainties for admissions offices. On the other hand, if admission can be plausibly offered to a student who is unlikely to be admitted to any other “top” school, that student is more likely to come, and the admission makes filling the class to the desired numbers simpler.
But then as a side effect, students learn about the profile of the single-top admit student, and more of them essentially match that profile than can be accommodated–so they develop unrealistic expectations of their admissions chances.
Of course, I can’t prove this, because I don’t have the inside scoop. But it at least makes some sense.
On the other hand, I suppose the simplest explanation for unrealistic expectations can be found by applying Occam’s razor: People tend to overestimate their own excellence. (This holds for most Americans, I think. It does not hold for most British people, in my experience, Twoin18.)