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Hi Jim,
It is very difficult to do but the way I have been able to realize my cruising dreams is to live as debt free as possible. After my illness, we had to downsize since I lost my job. Fortunately, we owned a small cottage on the coast of Maine (800 sqft) with no debt. I had to do some work to make it year round but since I was out of work, all I had to pay for was materials. My work progress was slow as I had been a "white collar" guy for all of my adult work history.
We sold the cars we had loans on and purchased decent used cars. Saved us a lot on payments, taxes and registration, insurance, etc.
I purchased a Westsail 32 that needed lots of cosmetic work. All other systems were updated including engine, sails and rigging, tanks, etc. One more winter of work and the vessel will look like it looked when launched in 1980.
We will not sell our cottage for the reasons you described in your last post. We don't want to box us out of ever coming back on land. We will rent the place if we have to so that it can pay for itself on taxes and upkeep. We know if we sell it, we may not be able to afford it again. Even if we don't come back here to live permanently, the equity we have can be used to purchase elsewhere if we fall in love with a different area.
You last comment about retireing at age 68 is a tough one. I don't have an answer for your life some 20+ years from now. The problem of not realizing your dream is that it becomes huge regrets when and if you reach 68. What I have learned the most through my fight for life is that living is only "today". Sure there may be many tomorrows but those are gifts not yet realized.
You never know what can come to you unless you put yourself out there. Lin & Larry Pardey never looked back in their decision to cruise and made a pretty good living at it. Sure, they are an exception... or are they?
Good luck on your path.
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