Hi Mae!!
You asked about who has traveled during September before..we went last year (2007) in September and it was a great time to travel for us! Although I will say, it was a bit hotter than I expected at the end of September but that just meant we could eat more ice cream!!
Travel insurance? Not sure you need it for the hurricanes as much as you may want to consider it because you have kids!! There is no telling when they will get sick and may not be able to go, you know? I'm not a big insurance person but I felt like the extra $120 or so, was my security that we would be going to WDW!!
Know what I mean? I hope that helps!
It is like planning a wedding all over again, but less stressful, kinda!! Btw, meals....check out Chef Mickey's for the kids, we loved it there and Le Celliar for your FIL birthday...they are the best!!!!!!!
Take care!
Kristen