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East Coast Jan 2015 - itinerary, weather & risk

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Ok, my wife, 7yo son & I have a 5-week window starting Dec 26 through to late Jan 2015 that we'd like to have a family holiday across the US East Coast.
After arriving in NYC, the plan is to use the train to visit Boston, Philly & DC. From there we would head south, driving from Charleston, Savannah before reaching Orlando (taking in DisneyWorld that week between the Marathon and MLK weekends) . We'd then fly across to New Orleans, then back to NYC for a few nights at the end of January before the long flight back to Australia.
We accept it's going to be cold (freezing!), but I'm wary that the weather at this time of year may wreak havoc with our holiday plans in terms of flight delays and cancellations.
Have I done enough with the itinerary above to reduce this risk (e.g using trains in the colder areas at the start), or is a holiday to the East Coast in January just too much of a gamble with the weather?
Appreciate any advice or comments

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