If I lived in Wisconsin, I too would be looking for a warm weather location that I could keep my boat to escape the winters. We have done this numerous times. However, we normally find a "cold" weather climate to keep ours as we normally live in warm weather.
We used to keep our Catalina 25 on Lake Lanier in Georgia while we lived in Florida. We used to love to go up in the winter and enjoy the snow. Remember, we got to go home to where it was warm when we got tired of it.....
Now we keep Karma, our R-29, in Port Orchard Washington while we live in Henderson Nevada.
You will always run the risk of someone screwing with your boat whether you live 2500 miles away or 10 miles away. Its just the facts of life unfortunately. When we kept our Catalina 25 on Lake Mead, 10 miles away, someone stole our BBQ. We only left it mounted once.......
If you should decide to take on such an adventure, a couple of things to look at:
1) Good airports. We fly out of Las Vegas to Seatac in Seattle. You will need the same to keep your cost down. If it is too expensive, you will limit your "boat time".
2) Good ground transportation. We take a cab to the Seattle/Bremerton Ferry, then take the "foot ferry" from Bremerton over to Port Orchard. This puts us within a 1000 feet of Karma. If you don't have good ground transportation, you will need to have a car on sight (additional cost.....). Now you will need to find a place to park long term at the airport. Normally $8.00 to $14.00 per day. That will add up quick.
3) Get to know your neighbors in the marina quickly. If you feel they are trustworthy, tell them of your plan. Keep boat here, live there..... Also, get to know the marina staff. Let them know when you are leaving and when you expect to return. Make sure that if you trust your "neighbors", give them contact information on how to reach you in an emergency.
4) Secure your boat with GOOD dock lines. You will be away for maybe four weeks at a time and you want to know that it will still be tied up when you get back......
5) Get good insurance just in case......
6) Buy your R-29 from Gene down there in Florida. Find out what the closet marina is to his office. Become his best friend...... You will have to remember though, summers in Florida=Hurricane..... not good. You will need to move the boat north in the summer to avoid VERY high insurance.......
There is nothing wrong with your plan. Find your location and make it work. You will love it!
If you would like to talk more about this subject, send me a PM and I will send you my Cell Number.