I can't vote, because I like parts of many answers, but not the answer, inclusive,
Out of the March-May, we like later May... not as crowded, the weather is consistantly warm, and there is little rain.
Out of the June - August, we like mid August. Hot, yes... rainy... pretty much everyday, but the crowds are pretty low.
Out of the September- November, we like the 3rd week of October. The weather is still pretty consistantly warm, the threat of Hurricanes has dwindled and the crowds aren't too bad. The golf tourniment is over, and the Food and Wine Festival, as well as
MNSSHP has begun.
Out of the December- February we like the 1st 2 weeks of December. The weather is iffy, which for us is a drawback... we like warm to hot weather, but there is usually little rain, the Christmas decorations are gorgeous, and the crowds are low.
So, sorry, I really can't answer your poll.