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82Venture,
Don't give up so easily. You did not say that you already charter with Moorings. Dependent on how many trips you take a year with them, it may work for you. An investment *( I know a boat should never be considered an investment) that can act as a second home and a rental property can work. The restrictions on how many weeks you can use a charter boat are different than a home rental from what I understand.
I would get on some of the charter sites, and more importantly the owner sites, and see what their experiences are. You will find some that think it is a great deal, and some with horror stories. Many people treat them as leases and roll them over as they go. Depends what you want at the end of the charter agreement. It might make business sense for you IF you will use it enough and you are in the right tax bracket. That is one for your accountant.
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