>>7521403I've actually never flown in or out of the airports other than Newark. I've heard they're pretty bad.
>>7521406A Christmas visit is really fun. I did that with my family when I was about 15 and it's what really made me fall in love with the city. If you visit though make sure you don't spend all your time in midtown though. That's where all the main tourist attractions are but try to take in a jazz set or comedy show in the Village or just spend some time wandering around Chelsea or the beautiful brownstones on the Upper East or West sides. Or check out the breweries in Brooklyn.
The homeless situation isn't really any worse than other large U.S. cities and quite a bit better than the major cities in California imo. Yes, you should probably be prepared to see homeless people pretty much anywhere you go in NYC, but as long as you walk quickly with a purpose and don't make eye contact or stop for people who try to talk to you then it's usually not an issue. Wear headphones if you're walking by yourself, even if you're not listening to anything. Don't gawk.
Probably the worst thing about the homeless population in NY is that they don't have anywhere to go to the bathroom so most of the city reeks of piss in the summer.