Greg; We were in a similar position several years ago and debated buying a place in the warm south. Then a friend told me to rent instead (I use VBRO); We tried it out and love it.
Advantages:
1 - different place every year - different view every year.
2 - when the lease is up you hand back the keys and leave
3 - no maintenance/up-keep when you are not there
4 - no worries when you're not there
etc etc.
we will be "touring" the south next year by renting a different house/condo
each week - again VBRO makes this really easy.
We're still fairly young (60) - and somehow I'm not sure we will ever buy a place in the south but it is a great place to visit during the North-East winters.