As an adviser and former adcom, when a student is doing something that most schools do not recommend, I think it is worth commenting on. This is particularly true when he/she mentions reusing the same items from last year indicating that at least some items have not been improved. Therefore it is worth bringing up to the student something he/she needs to critically analyze prior to reapplying. While this may be up to the individual, many medical schools specifically warn against applying again too soon (see below). This is the same concept that you will use as a physician when a patient comes in for one thing but you suspect another. So if I can help the student by providing this critique, thus helping him/her be a 3rd time reapplicant, I shall
University of Miami Miller School of Medicine
http://admissions.med.miami.edu/md-programs/general-md/reapplicants
Roughly 20% of the students who apply to the University of Miami Miller School of Medicine in any given year are reapplicants. Data that we have collected indicate they have a lower acceptance rate than do first time applicants
University of Wisconsin School of Medicine and Public Heath
http://www.med.wisc.edu/education/md/admissions/reapplying/31716 (emphasis in the original)
There should be significant improvements in your application before reapplying. This might mean not reapplying the very next year. The most common error made by reapplicants is that they submit their next application too soon.
The Ohio State University College of Medicine
http://medicine.osu.edu/admissions/md/tips-and-advice/pages/index.aspx
To maximize the chances of giving off this perception, you must allow enough time before reapplying. This will undoubtedly be the hardest part of the process, but be patient; if you rush it, you may join the ranks of those who are applying for a third time.
University of Minnesota Medical School
https://www.med.umn.edu/admissions/how-apply/re-applicant
Though you can submit a second application immediately after your first application, you may want to consider waiting a year if you feel you need more experiences that help you demonstrate the essential and desired qualities of an ideal medical student.