Next year (2001) will be leaving home base of Florida for 5 months and staying in the US for a change. We will drive a BIG circle, including a month in LA and a month in New York at the two ends of the trip. One in May and one in September. I think either month is LA would be a toss-up having spent both those months there before, but what about New York? Is September likely to be rainy and starting to get too cold? Or is it more alive particularly with cultural events than in May?

Both times of the year are great! I would choose both!

September is prime hurricane month.I would choose May.

Patrick,
L.A. and NY? Doesn't sound to me like you'll be staying in the U.S.

Seriously, Spetember is my favorite month here in NY, and hurricanes are rarely a disruption.

Weatherwise, both are among the best of the year in New York. So, that's a tossup.
Culturally, however, May wins easily. May is a peak cultural season. The theater season is at its zenith. New shows have opened to beat the deadline for Tony nominations, and others are hanging on in hopes of winning a Tony or two! At Lincoln Center, you have a choice of two of nation's premier ballet companies--American Ballet Theater and NY City Ballet--plus opera and symphony. Conversely in September, the cultural season hasn't kicked off yet.
(P.S.: What hurricane season??????)

I live in NYC and we had a hurricane here just last fall but fortunately it didn't really cause any problems.

It's funny, I had been telling people that one of the biggest advantages of living in NYC is that we get very few serious natural disasters...then I saw something on the Weather Channel website which said that NYC is very likely to get hit with a hurricane at some point and is extrememly vulnerable because it would be very difficult to evacuate.