Since you've obviously got your head screwed on straight, you'll be welcome in Florida. I grew up in Florida and just moved back about three years ago. I looked around long and hard before deciding where to settle and decided on North Florida. Very conservative part of the state, (it's our job to offset all the DemoRat condo commandos that live in southeast Florida), and housing prices are still very reasonable, (coming from NY you'll probably think they are positively dirt cheap). But, the real estate hucksters triple the price of any property that can even see the water (even if it's only a puddle).
Jacksonville is a banking center in FL and your son could probably find something productive there. The Jacksonville / St. Augustine beaches are expensive property - but, you can easily buy a large 2500 sq foot house 30 minutes from the beach for less than $200K. Since you're retired, living in the outlying counties could reduce that price even more. Property taxes in Florida are very reasonable IF you stay away from the beaches - I would guess you could plan in about 1.5% of the house's value each year. Sales tax is 6-7%, depending on the locality. NO state income tax and when you register your car in FL, they charge some ~$20 registration fee and a new license plate will be about $100 ($40-50 a year after the new plate). There are NO personal proerty taxes on your car(s), so you won't get a bill for $400-500 after you register your car - but, you will pay sales tax if you buy a car. Florida DOES require minimum auto insurance -- and Heaven help you if you get stopped and don't have proof of insurance. You have to get a Florida Driver's License within 90 days of arrival -- if your out of state license is still valid, no test, just pay the $20 fee.
Living on the beach WILL be an "adventure" in a hurricane - imagine a 10-15' wall of water paying you a visit with 20' waves on top of that (it's called storm surge). Not much can stand up against that - DO NOT plan on staying at the beach if you're expecting a Category 2 or higher hurricane. It can easily be a life-threatening experience, not to mention the fact that property tax insurers also know these facts. But, storm surge is not much of an issue if you live 4-5 miles inland and NOT on a river or big creek. Florida is building new homes to a hurricane resistant building code, my house is built to withstand winds of 120 mph. It does drive up the house cost by $2,000-4,000 - but, it's well worth it when your neighbors in older houses are looking at serious damage and you're hardly scratched?
If you're looking to stay with like-minded folks, I would suggest North Florida or the panhandle. Stay away from Gainesville, college town full of liberals who never met a tax they didn't want to raise for some stupid program or another. Southwest FL is fairly conservative (Naples and Sarasota) but propery prices are kinda high. Southeast Florida is over-run with NE liberals and you wouldn't like it very much (anywhere south of Vero Beach).
As for the weather, the Chamber of Commerce types say it best -- "Winter in Florida is beautiful, particularly if it falls on the weekend!" Hopefully, all this was helpful?
Absolutely!!! Thank you so much!!! If my mother was still alive, she'd probably question you about having my head screwed on straight ;-)