So far I think the Charter thing has been great, but its all in the "fit".
You mention, "I've got six years before my kids head
off to college, and we've already told them that once they're packed and out the door on the first day, so are we." That was our inspiration a couple of years ago. We also, were less than impressed with the math that charter companies, as well as land based properties, were pitching. It always seemed that the charter revenue was enough to cover either the mortgage or the depreciation, but never both, and there seemed to be too many variables that could go sour.
Added to that, finding the right boat, the right location, and a well respected charter company with an opening, is a lot to ask.
For us, when the "fit" came along, we couldn't say no.
The Moorings 3800 Cat is our #1 Choice of boat for a zillion reasons. (different thread...)
With a down payment, that was affordable to us, we struck a deal where the guaranteed revenue matched the monthly costs and a preset trade
in value put a bottom depreciation.
Moorings just happened to be planning a new base, using Cats, in the Carribean, just down the coast from where my cousin just bought a condo.
We chartered with Moorings in Tortola and got a look at boats in Footloose (Mooring's 2nd tier) that had already been through a full charter cycle and were impressed with their condition.
We spoke to as many people as we could find with both charter and ownership
experience, regardless of company, and found a healthy respect for Moorings.
We are relatively new to big boat sailing and need the experience before "going it alone" and currently don't have more than a couple of weeks a year to sail anyway.
If you factor in expense alternatives like the cost of beach front accomodation for the annual family
holiday (without a boat), then things start to look really good...