never experienced a day over 80 degrees. Plus, there's usually a breeze.
But you do cite a problem, that if one dresses strictly for water temperature, you may overheat in the air.
Nutcase that I am, I forsee a time when solar powered pumps force outside or even water cooled air through drysuits. Until then, I would compromise. And, I think you have to plan as if you are NOT going in the drink and NOT struggling with the re-entry issue.
Pull-Up Strap Handle Kit
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