Train for an early in the year or later in the year IM distance race

Looking for some insights from those who have completed long distance events.

I know allot depends on which actual event you want to do and go to, but which do you feel is easier, better, funner to train for? An event in Feb--April where you train throughout the colder winter months or a Sept-Nov event where you train throughout the warmer summer?

Figure throughout the winter you don't get over heated but have to deal with the cold, have to swim indoors, and actual event will be hotter than most of your training. Of course then throughout the summer will mostly the opposite. Able to do any type of training, but heat will be a problem, but might not as bad in the actual event

BTW I live in Florida so the winter cold and summer heat is different than most more north of me.