Ooh, Ooh, pick me, pick me!!!!!!!
We have been flying to FL from either BOS or PVD for the past 8 or 9 years. Some years we have NO bumps in the road whatsoever. Other years, our trips are challenging, to say the least, and have been 'well documented' here on the Transportation Board.
Our WORST experience was the Valentine's Day storm, the year Jet Blue had their epic melt down. We were flying Delta, and were scheduled to fly out on Wednesday morning. We spent about 8 hours at the airport, boarding and deplaning, until the flight was ultimately canceled. Delta could not re-book us until Saturday night! And, they could not get us into Ft Myers, they got us as far as Tampa, and we drove the rest of the way. So we missed 4 days of our vacation. However, we stay with my parents, so we did not lose out on any hotel fees.
Last year we were supposed to fly the Wednesday before School Vacation, and they were predicting blockbuster snow in MA. My cousin and her family were scheduled to fly the day before us on SWA, and got canceled Monday night for their Tuesday flight. They were connecting through BWI, which got HAMMERED. She called me, and we scrapped our plans to fly, figuring nothing would be getting out of Logan the next day, and we rented a Chevy Tahoe, and drove. 4 adults, 3 12 year olds, 29 hours.
With the way this winter has gone, we hedged our bets, and rented a car a couple of weeks ago, just in case.
So, my advice, is to read through the "What to do if your flight is canceled" thread, start exploring some other options, and keep a 'weather eye' on things.
If you're flying SWA and the weather is BAD in NE, look into possibly renting a car one way, driving the 5 or so hours to PHL, and flying out of PA? You'd only be paying the difference in fare, and if it's weather related, I wonder if SWA would work with you?