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Not really a sailor here, well, not at all. But, I do have lots of sailing in my family (all grandparents), and I've lived much of my life on freshwater lakes (Great Lakes and area).
While I still have my grandparents around, I want to have them teach me to sail. I think we would both benefit from the arrangement.
Life is short, and there is only so much money and time to go around. But, one of the dreams I would love to fulfill would be a relatively large ocean-going trip.
OP - what kind of sailing are you interested in? How much money do you think you'll need to keep it all running?