After the 5 years are up you will have tough decisions to make. You will now own a very used boat and still have a mortgage on it that will be upside down. What now? Put it in another charter option that will be a net negative situation? Keep it as a private boat that will also have additional expenses including insurance and boat care, new sails, slip fees, bla bla bla etc. Don't get me wrong it has worked for us mainly because the boat is used by one of us probably a total of maybe 180+ days every year.
That's what I mean by take a very hard look at what happens after the 5 years.