Obviously one of the main concerns is financial. Can you afford to buy a second home and will you be able to afford to maintain it? Everyone is different, in our particular case, we had money in our 401K, it was not earning a lot and taking out some of it to pay in cash for our Florida home was a good decision. Not having a mortgage is a good thing.
You need to weigh the security of having all your money in your 401K against the benefit of investing in real estate. I can tell you that the value of our home has doubled in six years and that is a lot more money than we would have earned with our investments. Finding a good buy is important and prices in Florida are much more affordable than they are up north, at least in New England.
Many people opt to make Florida their main residence, it is a much more friendly state to seniors than most northern states. Georgia is even more friendly. I have cousins who opted for Alabama. You do have choices and I recommended renting in a variety of locations or at last staying in hotels in a variety of areas to find out what you like and dislike. Attend the local church which if you attend church is mighty important, see where the grocery stores are located, etc.
Make sure that there is an airport convenient to the location you choose. We didn't think about this and unfortunately, Ocala does not have a commercial airport. We have to choose Orlando, Tampa, Gainesville or Sanford, all of which are a good distance away. In spite of that, I love Ocala, it is horse country and has a different feel than other places in Florida.
You need to decide exactly what you require in a winter home. How many rooms, bathrooms, home vs condo or manufactured home. Do you want a gated community or ungated? As a snowbird your home will be unoccupied for months, will it be safe? Do you want to rent when you are not using your winter home? Make sure that it is allowed where you are buying. Renting can help make having a winter home affordable.
If you are tired of shoveling snow but have grandkids you can't imagine moving away from, full time, keeping two homes is an option to consider. At the end of the day, it makes better financial sense than renting.
