Ten days to go is an important mark when you are waiting for any vacation. When you hit ten days you can start to check the weather. Most people would check the weather at their destination. However, for anyone who lives in New England, the destination comes second. During the winter you always check the local weather first.
Why would you check the local weather first? Because booking any airfare in the winter is a gamble. You cross your fingers and hope a storm doesn't hit the day you fly out. Thankfully I've never had a storm hit the day I've had to fly out. My wife however has.
What do you do if a big storm is going to hit the day you are trying to fly out? You gamble. To put it simply you book another flight for the day before and book a cheap hotel at your destination. This is a gamble because if the weather isn't bad enought to cancel you get stuck paying for two flights. Granted you only do this for slam dunk storms. Normal storms you keep your fingers crossed and hang out at the airport.
You might wonder why you wouldn't just buy travel insurance. I do buy travel insurance but I'd rather enjoy my vacation than get reimbursed for lost days. That's an awful way to start your vacation.