Just a quick post this time. In my continuing research on the money issue, one of the best "answers" to the annual cost of cruising question I've found was in this article from the Beth and Evans site:
Cost of Cruising
They have collected real user data and created three fictitious families to demonstrate the average annual cost of living and cruising on a sailboat. Obviously everyone's situation will be different, but this article written in 2006 seems to be a reasonable starting point.