I'm always so surprised when people mention BUGS as a reason not to live in Florida. That's truly the least of my issues with Florida. Having lived in Southeast FL for 25+ years we seldom, if ever, struggle with bugs. We have a pest control company that treats once a quarter and NO bugs in the house. Perhaps in more rural areas, bugs may be a problem, but not in the urban areas.
The humidity, now that's an issue, especially in the summer months. But it's really quite manageable, even in the summer. Just stay indoors from about noon to 4:00 p.m. As Ron mentions upthread, we have three AMAZING months of weather and six good months of weather. That really just leaves three months of brutal weather.
I can pretty much travel during June, July and August and we can basically choose where we want to be those three months. We generally spend the month of June traveling on pleasure and the month of August on Cape Cod, so that leaves July. We usually spend a week in Hilton Head in July, but the other three weeks in South Florida. We choose to spend those three weeks in South Florida over NYC. NY is just miserable for us in the summer. The restaurants are not air conditioned, the subways are hot as hell, and too many tourists reading maps. FL has "proper" air conditioning.... not matched in many places...
Hurricane Irma has me really questioning our long-term plans in retirement. The idea was to have a place on the water on Hilton Head for May - September and winter in Southeast Florida. I'm just not sure now. We've lived through many hurricanes, Andrew, Irene, Frances, Jeanne, Wilma, Matthew, and now Irma. We were SO lucky this time.... The way that the storm was predicted, Palm Beach County was going to be decimated. So, bugs, humidity, traffic, and such really don't make me not love living in FL, but these storms are really not good... Maybe our plan should be summer in Hilton Head and winter in Henderson, Nevada. I've got about 20 years to figure that out, a lot could change in that time...