Well. September is a good idea, but if you can push it to later than earlier. All the schools will be back in session, and you will be able to do MNSSHP as well as the FWF. Don't know if that will coincide with free DDP though.
The hurricane season is more problematic than the "usual" weather actually. If one blows in, you're running a real risk of having your holiday interfered with. I'd not go over the top worrying about it, just something to consider.
Sometimes the lovebugs (as this year) are barely noticeable. They are very light this year.