Hi TropicalGal,
We have been going through this exact process since January, but our time horizon for cruising is more like 3-5 years. Personally, I feel buying a pre-owned catamaran and chartering it for several years is a good strategy (obviously), but to be successful in chartering it can't be too old. Are you looking at new boats like with Moorings/Sunsail, TMM or Horizon? That's the only way I'd do a 10-year charter life (5 with first company, 5 with second company). That's a loooooong time to have your boat in charter, it will get a lot of wear and tear.

Before making this decision, you need to research the different brands and charter companies. Go to boat shows, look at what they're bringing out. Ask surveyors and maintenance people which brands have more problems. If buying new, do it through a boat show special price, where you'll probably get your best deal. We didn't buy new because I didn't want to take the 45-55% depreciation hit in 5 years. We're buying a 2009 Leopard 46, not too old, should be still good for chartering for several years, and a great boat for cruising as well as chartering.

Most popular cats to charter: Leopard and Lagoon seem to be, but you also have to think about blue-water capability since you plan to cruise. I wouldn't cruise on a Voyage (bridgedeck too low) although they seem popular for chartering. I've only seen them chartered in the BVI.

Lastly, 3 weeks annually is about the minimum personal usage you should do. Personal usage is a key factor in making the economics of charter boat ownership work for you. When we evaluated the new boat program with Sunsail, we had difficulty making it break even unless we used it 4-6 weeks and saved those chartering costs.

Rob