I'm about to turn 39. We live in the SF bay area and have great jobs, dual income, no kids, no debt (no CC, school loans, nothing). Our vehicles are all old and paid for, we save money every month. Sadly we live in an area where there are too many people and not enough housing. Rents are insanely high for even a modest place to live. Sales and fuel taxes make everything more expensive. We do OK but we have to be careful. God help us when we want to have kids.... in most other parts of the country we'd be living well at our income level. Not here. If you're older and you bought your house in the 80s and 90s you're doing great. if you bought lately... well... you're spending most of your available income paying a mortgage that 2-3 maybe 4x what your older neighbor pays. Salaries have not kept up with inflation and the rise of living expenses.
I think that good sailing areas tend to be high demand areas to live and the cost of living is very high. If you're a younger person with a mortgage you just can't reasonably justify a boat loan. If you're handy and have time to put work into it you can support an older boat. If not you can't afford the loan or the maintenance costs.
Someone please tell me where we can live so that I can get a good job with computers, support a family, have a reasonable cost of living, and still have a nice place to own a boat and sail. Any country will do. We dream of this life all the time...
You've got the right idea. Stay out of debt. Debt is slavery and affects all area of your life. Worrying about debt is the #1 cause of stress, depression, etc. It is surely a VERY bad idea to get in debt for a sailboat. As others have indicated, there are lots of very good old boats to be had in this economy. The expenses involved in owning a boat are high and should be in the "paid for in cash" category.
If you are making good salaries, keep saving, and employ "sweat equity" in everything you do, including a house. As far as living in a place with low housing costs, there are many. It's all about supply and demand. You may have to look on the outskirts of attractive areas and do some long commuting. Paying an extra couple of hundred bucks for gas each month to drive to work is a small amount compared to paying a thousand or more for rent in a place in the center of a high rent district.
If you find a place where you like to work (the majority of your waking time), like the people, the place, the salary, etc. This kind of career move should be the main concern. It is often wise to then find a house within driving range, in the outskirt zone where prices have not yet gone through the roof and the house will more likely gain in value. Don't buy some crappy tract house, built by a developer, build it right and do it yourself, even if that means simply hiring local contractors to do it.