Don't do it. If you don't like hot weather, you're going to hate living at a dock where you can't control the air temp or the wind howling through the rigging all the livelong day and night. You'll hate not having less access to the grandkids. Sailhog's advice: create a situation where you have a nice little condo and inexpensive access to your boat, which you can sail south or north or wherever you please. Take three months next November and cruise to Florida, Bahamas, and then turn around. See what it's really like to camp on your boat day-in and day-out for an extended period. There's little to be gained by jumping in feet first, and the downside risk is real and, in my opinion, significant. What do you come back to if something happens to the boat? What if the money dries up from investments that don't work out as planned? What if there's a family emergency? Keep your boat, sail your ass off, come home to your itty-bitty condo and enjoy the grandkids. That would be a good life to live. Fantasies have a way of turning into nightmares. Do what's do-able.