Susan:
Tough call. Both sets of dates have pros and cons. But I think I can help you feel better about going with your gut on the September dates...
You listed humidity and hurricane worries for the dates in September. I've been twice in September and have had short, afternoon showers, but never a hurricane. Yes, it is usually warm, but that makes for weather that allows you to make the most of the pool and leave the light jacket in the room when you venture out at night. What makes September especially appealing, though, will be the slightly smaller crowds in comparison to the Halloween weekend crowds of your second dates and most especially the
free dining offer that's going on right now for those dates.
Our family has also visited twice during late October/early November and are making plans to be there for Halloween again this year. We love the cooler weather that fall brings to Disney, but keep in mind that its regular season so crowds are thicker and prices for rooms more expensive. We choose those dates over September because of our school schedule and the fact that we love to be at Fort Wilderness in our RV for Halloween weekend activities.
Harvest decorations will be up for both dates throughout the parks and resorts, so you'll be paying for cooler weather with your October and November dates, that's about it, while you potentially miss out on smaller crowds in September and free dining. Which leaves us hurricanes. I live about 90 miles from where Hurricane Katrina hit. There are very few each season in the gulf. And even fewer that make it to the Florida coast. I'd consider using a portion of
your savings to buy trip insurance for piece of mind if it's a big deal and put the rest aside to splurge on your September trip!
Wishing y'all a magical vacation!
Whitney