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Anybody at Penn know how admissions feels about a letter of interest? It's been several weeks since I submitted my stuff, and I know some schools really appreciate them.
An interest letter certainly will never hurt you. For Penn, my opinion would be that a significant update letter (publications, leadership activities, unique circumstances) would carry more weight for your application than a statement of your interest. For interest/intent letters, I feel that it's probably better to send them later in the cycle (provided the school is non-rolling), because while a certain school may be your top choice on this date in October, the school has no way of knowing if that will hold true after a few more months of interviews, etc... If you send the same letter in late January or February though, as most interview cycles are wrapping up, it would seem to carry more weight. In the event that you are waitlisted though, at that point, it is almost imperative to send interest/intent letters, and I feel like they carry the most weight in that situation.