Passive Income - yachts?

[Allison Karrels]

Small back ground: My husband and I own 8 SFH that we use for monthly passive income streams. My husband is in the Air Force and plans to retire in 8 more years. Between his pensions and our rental income we will have great monthly income flow. We both love water and boats and plan on sailing once retired and eventually sailing around the world.

Plan:  We originally thought we would get to 10 houses and then pay them off so our cash flow is increased in retirement.  But now we are seriously considering buying a yacht from "The Moorings", allowing them to use it as a charter boat for 5 years and then taking ownership of that boat and using it as our main sailing boat/house.    During those 5 years they are using the boat they take care of every expense and pay you a guaranteed monthly income above what the boat mortgage payment is.  In most cases a few hundred dollars more than the mortgage.   You also get to use your boat 12 weeks out of the year (mix of high and low season weeks) with only a small turnover fee.

Question - Are we crazy?   Does anyone here have experience with owning a Moorings boat or doing a charter vacation with them?   We plan on doing a charter with them next year and if we did buy a boat with them it would be 2-3 years down the road so it lines up with my husband's retirement.   We just thought it was kinda cool we could own a boat, get it paid down over the first 5 years, get to vacation on the boat, etc before taking ownership back.  It would be a 15 year mortgage and if we applied the extra money each month to the payment we would have about 7 years remaining on the mortgage when we took it over. 

Thanks for any input.