Trish and I have been living aboard since December 05. I purchased an Island Packet 40 for a 2-3 year cruise of the Caribbean. We lived aboard dockside for a month and a half in Marco Island, FL before heading across the horizon to start our trip.
I chose a boat that was fully outfitted and in very good condition. With the addition of some charging (wind and solar), she was ready to go. I have had no regrets and no major problems on this boat. Fuel and water tankage are more than adequate. Storage is more than adequate.
With extensive systems, she is a chore to maintain. However, I have the skills and knowledge to do so and generally enjoy it. There have been a few instances of frustration, but I wouldn't do it differently.
I'm 34 and Trish is 33. I worked 80 hours a week, always with the dream in mind, paid cash for the boat, and never looked back.