We definitely wouldn’t trade our 15+ years of cruising and living aboard experiences for anything - it was very enjoyable even with the problems which are inevitable. We saw many beautiful places, met some fine people, made lifelong friends and have many fond memories. When people tell us they have always dreamed of living on a boat, I say, try it...what’s the worst thing that can happen? If you decide you hate it, then you can always sell and try something else. But at least you did it.
Your friend can always buy a smaller house on the water somewhere and keep a boat docked behind it for trips. Ft. Lauderdale is a wonderful place to do that as is the Gulf Coast of Florida like Venice, Longboat Key, Sarasota, St. Petersburg, etc. Another idea is buying a house in the Bahamas. HGTV has a program called “Living the Bahamas Life” and there is a big variety of homes at all different prices throughout that island chain. Many airlines fly there now, for example, Marsh Harbour, Freeport or Nassau so family can come visit. There are plenty of options for your friends.
It's amazing the difference in people and how some love something others can't handle. I'm like your dad, I get nauseous on the ocean, even on a glassy sea.
They do the cruise ship thing every year, and I've been with them on a boat off the Alaskan coast looking for whales. He was all over the boat while I was staring at placards inside the cabin, trying not to upchuck. lol
Passing on your recommendation for a powered boat, in your other comment.
Thanks!