Applied: 7
Accepted: 5 (all with at least 5 years of funding)
Attending: Yale
I think a lot of good points have already been covered, but I guess confirmation never hurts:)
1. I definitely agree that fit is much more important than the name; Harvard, for instance, is a great place to do classics in general, but when it comes to classical philosophy, its program may not be as strong as other places. Similarly, Yale's department is quite literary, and perhaps not as strong in material culture. At the end, it really depends on your own interests.
2. I heard from a lot of people that reaching out to programs and professors could be an advantage in the admissions process, but unfortunately this wasn't my case: the only place I contacted was one of the two places where I got rejected. So it depends on the personality of the professor, and the culture of the department, whether reaching out helps.
3. For Berkeley, make sure you spend some (but not a lot) time on the personal history statement; I suspect that's the reason I received a prestigious fellowship there.
4. Most importantly, for me at least, you should know your strengths and weaknesses and try to craft your application in a way that emphasizes one and shows that the other could be easily improved. As an applicant, you could be traditionally strong, or you could be sexy. Someone with strong training, say 6 or 7 years of both Greek and Latin, who went to a reputable university, and maybe even have an MA, will most likely get into a very good school. But this doesn't mean you have to be that person to get into a top program; you could have a very provocative writing sample that challenges current scholarship, or you could have extensive exposure to one or two related fields, for instance. I don't have an MA; I have less than 2 years of experience in both Greek and Latin (though the experience was quite intensive), and I still got into many of the top programs.
Good luck to everyone!