Great dream - that many of us share. Someday, I hope to convince my SO that this is the way for us to start our early retirement.
I can't share any of my experience, but here are two websites that I have followed about people that have. The first is the blog of a guy in Toronto that lives (or lived) aboard year round with his wife and son on an Alberg 30. http://weliveonaboat.com/index.html
Read the archives, they are well written, and not too long. He hasn't posted in a while, so I hope that everything is OK.
The second is the website of Susanne Geisman. http://www.libertysails.com/
Susanne and her husband, Ty, decided to quit their jobs in DC after 9/11. They bought a Morgan 46-2 in 2002, and lived "the cruising dream" from 2003-2006. They rented their condo in DC to some college kids while they were gone. Her book Living a Dream
is an excellent overview of the process of making the decision, and acting on it. They returned to DC in September '06 to deal with a family tragedy, and then decided to refill the cruising kitty. Susanne currently does seminars on the boat show circuit, and Ty is a defense contractor consultant.
A third reference would be Beth Lenoard's The Voyager's Handbook
especially chapter 1. Check it out. You can read most of Chapter 1 on Amazon.com's see inside
link. She addresses crew (more than one) capabilities and motivation, and the assignation of tasks.
I hope these help you in your decision.
P.S. If I were single, I'd go for it!