My husband and I are asking myself very similar questions. We are close to your age, are fresh out of graduate school, have good incomes, and are asking ourselves: What now? I have far more questions at this point than wisdom, but here's something I've been mulling over --
1. In most areas, you won't save money by buying or living on a boat over buying and living in a house. At least not if you plan to keep the boat in good repair and want a solid boat. So when you consider house vs. boat in terms of investment, they break even or the house wins.
2. If you compare the cost of owning and living a house, plus owning a boat -- because let's face it, you love the boat -- to the cost of owning and living on just the boat, then the boat is far cheaper. You can cut out the entire cost of owning the house!
In view of number 2, I have been seriously considering the wisdom of getting a boat and taking all the money I would have sunk into the house and investing it ... historically, stocks have pawned property as investments.
In your case, you own a boat already. If you could live on it, you could always start there (no big outlay in cash for the 2010) and see how it goes.
Just a thought -- no doubt, in my own idealism and partial ignorance, I've passed over an important point.