September is much nicer than any summer month. October may be even better but you start having the chance of cold fronts. When planning a flight to Key West I found a link that shows lightning activity in Florida. Since that should correlate to thunderstorms and weather I will avoid it provides a quick glance as to better weather.
http://www.srh.noaa.gov/tbw/information/ltg/ltg2.gif and http://www.srh.noaa.gov/tbw/information/ltg/ltg3.gif September shows a reduction from the highs of June/July and October is even better. Another useful link to get a birds eye view of rain is here: http://adds.aviationweather.gov/radar/ Even this morning there is some on the mid south probably associated with a cold front passage but it is much less than I have seen in summer months. http://adds.aviationweather.gov/radar/ September and October are the two highest hurricane months but personally I would not try to plan around them. If one happens such is life...unless you have the gathering in Florida! Something to consider if you are planning a date change or permanent location. This may require a change from your typical banquet decision to one that polls the wider KR community. Perhaps it is all KR-netters or all Gathering attendees for the last 10 years or so. Regardless, weather will always be a factor. I am a VFR pilot and I stick to my limitations. You won't find me trying to penetrate a thunderstorm. Ron Lee