Interesting reading and here's my contribution:
Ducky, I commend you and your wife for trying something new and different. I once opened a fortune cookie and inside it was written "You'll never know unless you try".
Cruising as a lifestyle is very different than cruising for a vacation and maybe one would suit you better than the other.
As mentioned in previous posts, there is no substitute for hands on experience when you take command of a vessel. I was hooked on boating from an early age when I was a guest on my Uncle's boats (all power boats, BTW). When he sold his last boat, there was a lengthy gap between that time and when I bought my own little 19' cuddy cabin. In between, the passion for being on the water was such that I joined the USCG Aux to gain as much hands on knowledge as I could without owning a boat myself and that experience was priceless. The Coast Guard motto, Semper Paratus, meaning "Always Ready", became my motto as well. After the 19' got too small and the kids grew too big, was another time when I was off the water. As Michael Corleone said, "Just when I thought I was out, they pull me back in", I took up an interest in sailing and took ASA courses that gave me the foundation for sailing skills. I would rent daysailers but then I found Offshore Passage Opportunities at a Strictly Sail show which offered their members the opportunity to crew on larger boats. Again, the knowledge and experience I gained was priceless.
All of this experience prepared me for the day when we bareboat chartered a 39' sloop in the BVI. I was the captain and my now 2 grown boys were my crew and my wife did what she does best and made dinner reservations...
That was the best vacation we ever had and was also the best medicine for attitude adjustments. When sailing, there's no room in the brain for anything other than what is at hand and that gives you the opportunity to clear the head and feel very refreshed at the end of the week. We'll be returning the end of May for another charter and I've been thinking about this trip from the last time we pulled back into base. It's a good alternative to owning your own boat, which is the ultimate goal for me
Which brings me to the most important point....you have to do what's best for you. Let your head rule over your heart because when there's life and property at risk, you need to make the right judgment call.
Best of luck in your future endeavors.