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The following tips on the residency Match process represents feedback from several Internal Medicine residency program directors (via Dr. Kiken, from our Dept. of Medicine); this info likely applies to other specialities as well:

1. If a student scored < 200 on Step 1, s/he should take Step 2 early enough so that program directors see it.
2. The important letters are the ones from the dean and the department chair.  Other letters are of minimal importance.
3. Program directors like to see a sub-I grade, especially if the medicine grade is not great.
4. The personal statement is not very important.  Nevertheless, it should NOT be a summary of the CV.  There really should be something personal in it.  It should be shown to 2 people who will be honest with the writer.  Grammatical errors (the most common problem) make the writer look bad.
5. If a student failed a course or took a leave or had a problem, it MUST be addressed by the student or the dean.  Program directors like honesty.
6. If a student wants a residency in a part of the country where s/he doesn't know about any of the hospitals, s/he should email a program director in that area and ask for advice.
7. Students often apply to "best programs" as long shots, do not really think about going to them, rank them at the top of their list, and then unexpectedly get in and end up not being happy.  Students should rank the places they know and want to go to.
8. If you know you will want a fellowship, think in terms of geography.  People tend to get them in the city or area they trained.  Go somewhere that has a program or where the subspecialists have relationships with fellowship program directors.  Community hospitals are fine in this regard. 

Many thanks to Dr. Kiken for this excellent and timely info!