I'll third (fourth?) The Boynton/Delray area. Somewhat less expensive and downright cheap compared with NY. Good range of reef, big stuff, and wrecks within a 30 min drive. Nowhere has better access to the Caribbean than south FL.
I moved here from NY a few years ago and I think the cost of insurance is a bit overblown. Yes it's higher than other places but I save far, far more on taxes alone. This of course may matter less for someone who's retired depending on the structure of retirement income. Traffic stinks but tolerable if you avoid Miami. FL has its negatives but diving year round in a 3mm and never dealing with winter outweighs all of them.
I moved here from NY a few years ago and I think the cost of insurance is a bit overblown. Yes it's higher than other places but I save far, far more on taxes alone. This of course may matter less for someone who's retired depending on the structure of retirement income. Traffic stinks but tolerable if you avoid Miami. FL has its negatives but diving year round in a 3mm and never dealing with winter outweighs all of them.