For me, living aboard took about 20 minutes - it's something I always wanted to do, and planned for many, many, many years to travel down the ICW to the Florida Keys and live aboard for at least one winter before returning north to the Chesapeake's upper reaches and home. After six months living aboard, I found there were a few drawback, but mostly pluses. The only problem I have is I'm still married to the same woman I married more than a half-century ago and she wants no part of living on a boat of any kind. Now, at age 72 and damned near 73, there are some things that I physically can no longer do. Consequently, had I been a liveaboard for any length of time prior to this, the stark reality is there will come a time when you will have to move ashore again.
Now, I did run into a guy who I consider one of my many heroes - Captain Jack. About 30 years ago, Captain Jack sailed his 26-footer to the Florida Keys from Miami to spend a long weekend there. He never went back to Miami, other than to sell everything and move aboard the boat with his wife. She passed away several years ago, Jack purchased a larger boat, a 28-footer, and still lives aboard in Marathon's City Marina. Jack is 91 years old and still hitting on the ladies every chance he gets. He's a great guy, and I do miss him, along with all the other live aboards I bet there.
Captain Jack picked fresh flowers for all the ladies in the marina every morning. At one point I wondered if there would be any flowers left in the nearby park. Oh, and Jack rode his bicycle to the part to get the flowers, which was about a half mile away.