I'm ::slightly:: biased, too as I love living in NYC! And the rumors are true, NYC is a very progressive, liberal city, but so am I so works for me!
NYC's clinic experience is fantastic. I'll be starting my 3rd year after the boards (wish me luck!) and have already started working in the clinic and I feel like I already know so much more. Because of the sheer volume of patients and the population surrounding the hospitals, you just see so many different pathologies and you learn so much - it's truly rewarding and it solidifies everything you learn in class.
I've never been down to Barry but I'm sure it's gorgeous (in beautiful, sunny Miami), so I can't comment on it. I have talked to people from Barry and they love it and I know it's a great school. When it comes to strength of curriculum, I'm almost positive all the schools have the same, very strong curriculum (everyone takes the same classes) - that might be a difficult one to compare.
At the end of the proverbial day, it depends on where he's comfortable - where he feels would be a good fit. But, if you or your friend has any specific questions about NYCPM please feel free to PM me and I'll answer them for ya!