NYC is at the southern tip of NY, so NY roads should not be an issue. But Google map sends you up the Appalachian spine, so if bad weather is predicted in that area, you might want to take a more coastal route along the Eastern seaboard.

I am not a huge fan of the Weather Channel, but you can check your planned route on their Interstate Travel website:

http://www.weather.com/activities/driving/interstate/?from=breadcrumbs

If you do this every morning, it will tell you what the conditions are likely to be en route and is a godsend in a general way, though they won't be able to predict local conditions like trees down. This is why you have a radio in your car, and you might have helpful smartphone apps.

Your most dangerous issue will be ice. If you take I-10 to Jacksonville and then up I-95, you should pretty much avoid it. If conditions are better inland, you can I-10 to I-65 to I-85 to I-95 and avoid all of the mountains and a good bit of the snow and ice country, but you only save about 120 miles over the I-10/95 route.

Even on the southern route, you shouldn't be in too much hurry to get on the road in the mornihg since glare ice may have developed overnight. You will also need to watch your car's external temperature gauge since conditions can deteriorate rapidly below 33, especially after dark.

Pack a couple of good books, a big basket of goodies and a nice bottle of wine (or three) for yourself so if you do get caught in icing conditions or even snow, you won't mind just stopping at the next motel and waiting it out. The people who are waiting for you would rather have you arrive alive.

No state from Maryland south handles snow as well as the worst states north of Maryland.

Besides allowing for bad weather - are you willing to pay for parking? You need to figure $35 to $40 per night to park your car -and it is totally useless once you get to the City.

Have you considered other options that won't leave you with this albatross? Or are you planning on sightseeing on the way to and from?