What a great thread! I'd like to add that in the last few years I've noticed the airlines are much quicker to offer to waive change fees for rebooking, and/or cancel flights. So I have a couple of tips to add:
1). When airlines allow you to rebook for free by waiving change fees, it does
NOT necessarily mean the flights will be cancelled. In the last year I took advantage of rebooking, and also turned it down, both times with good results. You have to gauge the situation for yourself.
-This past weekend my flight out of NC (where my daughter goes to school) was on the list of cities where rebooking fees were waived. But I took a look at the forecast and decided there was a good chance the flight would leave on time, so I didn't reschedule. As the flight time grew closer I kept checking to see if it was going to be canceled, and it never was. We left under cloudy but dry skies and had an uneventful flight & connection to our home airport.
-This is in direct contrast with Florence where anyone who was paying attention could see it was going to smack NC all the way inland, as soon as they offered rebooks on those I was all over it. I can tell you the phone wait time in the beginning was short and exploded after just a couple of hours. (This is where and early heads up from Twitter comes in handy). They then later cancelled all those flights, but I had rebooked long before that.
So I think a little judgement goes a long way in terms of the weather.
2). Don't assume you'll miss your connection, either. My son was set to miss his connecting flight because of a delay, but the weather was crappy all over so he elected to try to make the connection (and possibly stay overnight- we do have friends there).
All the flights ended up delayed. Sometimes you can tell this by checking flightaware to see where that connecting flight's plane actually is. In his case, it was coming in a little late and ended up a lot late, so he actually made it home. This has actually happened more than once to me as well.
3). And finally, if there's a catastrophe in a main hub it can have repercussions all across the country because flight crews and aircraft are not able to reposition. Imagine my surprise when the tornado in ATL two years ago caused my Delta flight out of Montana to be canceled! Pay attention to the news, if your airline's hub has a computer problem or weather disaster it could reach all the way across the country to you.