Well, the question was "What have others done? What are you worried most about?". I'm not looking for people to analyze my life and comment on my choices.
That said, 60 years boating, thousands of offshore miles, no family to worry about. I'm 66. Oh, and my wife isn't family; she's a piece of me.
Wifey B: You are correct but important to know if other's activities are relevant to you. If you and your wife have thousands of offshore miles together and no family to worry about, then that does greatly improve your odds.
We couldn't and wouldn't as we've somehow crazily developed a large extended family and could never be without our land home to return to and enjoy them. We're typically 6 weeks on board, then three at home, then six back cruising and we repeat over and over and over.
When it often doesn't work out is when one spouse is far less enthusiastic about the idea than the other. It also doesn't work for some who just lack the boating experience. Then grandkids are a big killer to full time cruising. Couples find they miss them too much.
Those like you and your wife are the ones who do make it work out. I'm betting as others post who have done it successfully you'll find they're very similar to you.
As to us, we cruised and responded to hubby's famous theory of pain, a business theory he has and also for things like this. At 4 weeks we were always ready for more. As we neared 6 weeks, we looked forward to the trip home. After three weeks at home we looked forward to returning to the boat. A couple of times we've stretched to 8 weeks but then always been anxious for home and stayed there longer. This summer, due to travel restrictions, we haven't been home since we flew back to Italy on June 29 and we fly home on October 16. We've had an incredible time but we really miss those at home. We will stay near the rest of the year with short trips. We webcam with them and especially with my 7 year old niece, Aurora, who I love soooooooooooooooo much, but omg I want to be close to her and she in person how she's growing and swim with her and boat with her. I don't know when this family thing happened to us. If we were like when we lived in NC, mostly just the two of us, we could live on a boat and just fly there twice a year and to Myrtle Beach those same times and be fine. We were so independent and now we're so interdependent. That's why I asked you the questions and now know our issues won't apply to you.
That's what we've done and as to what we'd worry about, it's simple. Separation from those important to us, those we love. It's not our home that's the problem, it's the people at home. When we lived in NC we could have made the change easily, but not today.