Well, I just spent my first ever birthday in warm weather. Pretty sweet, walking on the beach and watching the sunset instead of huddled inside the house. Even good weather on my birthday usually meant sunny and pretty damn chilly.
However, as far as migrating to FL, I've recently been (and still am) dealing with some nasty insurance issues related to being a FL homeowner and resident.
Before I had my primary residence in VA, and a second home in MD. No problem, Allstate covered both, as well as riders for jewelry, flood insurance where needed, umbrella, etc. But once we declared FL our PR, we had to get a homeowner's policy with Joe's Insurance (Federated, really), because none of the big names do homeowners in FL. No big deal. But a bit of a pita. We turned the VA house into a rental, and it's out of this story now. So a couple of months ago my Mom died, and I inherited her house in VA, as well as her wedding ring. She was insured by USAA, but I'm not eligible for it, so they notified me they'll be dropping her insurance as each policy expires. So I called Allstate to see if I could add these items to my policy up there. That's when things went to hell.
Turns out when they cancelled my VA house as a primary residence, they also dropped the liability on the MD house. And the jewelry riders. And the umbrella. Because those things all hang off the primary policy. They can't insure a second home alone for those things if they don't have the PR. Federated can't do anything for me because they're mostly only in FL, and there are other details like the value of the FL (PR) house being so low and the value of the MD house being so high. And the one possible policy I found was asking for a $12K/year premium, which is insane.
Long story short, we haven't had liability or jewelry or umbrella coverage up north for almost a year, and we're having a huge issue trying to get it. I've talked to Allstate as well as an independent agent, and it's just not working out very well. If I could find a company that does homeowners in both places I'd switch to that, but no luck so far.
So, if you are making FL your primary residence but keeping another home, be careful with the insurance issues. Personally I think my Allstate agent dropped the ball by not letting us know about this when the policies changed last year, but I'm somewhat to blame to for not reading the policies. I will find a way to get this all cleared up, but it's been a big enough hassle that I'm considering changing my PR to MD. My income is low enough that the income tax savings of being a FL resident is being overwhelmed by the additional insurance costs. Nothing's ever easy, I guess.