Run_DMC1991

Historically we always went down a week or so before Halloween or the second week of November. We have never had cold weather. It has always been high 70's to 80's, with low or high humidity depending upon storm activity. Even on the humid days it has been generally tolerable. Way back when the girls were little we would go when they were out of school in January. The worst we ever saw was low 60's which for the locals might be cool/cold but was very comfortable for us coming from mid-40's to low 50's.
It sounds like a good idea for the first time to stay in condo. You could also take the boats from the MK over to the Fort to get an idea of what it is like. Once there you can take the internal buses, walk or combination of the two to get around. You could also plan a meal at the Hoopty Doo Review, Mickey's Backyard BBQ or Trail's End restaurant for when you are there. 

You never know in Florida, we are usually up there in early December. Most years it's been shorts and t-shirts weather other years we've ended up going to the outlets and buying warmer clothes or sweatshirts at Disney. 
 
If you're thinking of staying off property here's a link for a place we used to stay before we got our trailer.
 http://www.lbvorlandoresort.com
They have 2 and 3 bedroom units some with fireworks view. Not a bad drive to Disney though S Apopka Vineland gets pretty backed up around rush hour time. The resort was always nice they have 2 pools, one with a pirate ship slide and bar. 
We also stayed here http://www.likitiki.com/?mkc=googleus a few times but the last time was probably 8 years ago or so and I think it might have still been the Ron John resort back then. It was nice and had a great pool for kids and bar for adults. 
Just a couple of ideas if you didn't already have something in mind. 

I have a camping list that I use for all our camping trips.  Some may think it's crazy but I don't want to forget anything!  I modify it with each adventure.  
2016 Camping List.xlsx

I forgot to add a tarp large enough to go under the tent as a footprint. This helps keep the tent floor in better shape and isolate it from ground moisture. Just be sure none of the tarp sticks out from under the tent bottom or it will result in water pooling underneath.