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We are on about the same time frame as you, however we will purchase a smaller sailboat over the winter.Something expendable that we could take a loss on or just keep at the lake house for the family to use. Between the sailboat and the "stink potter" we already have we can learn everything needed, except the handling of a larger boat. Everybody that already has a stink pot can use it to learn lots, even before purchasing a sailboat. Knots, navigation, gps, chartplotters, radar, engines, electrical, and don't forget radios.
Legal issues? maybe visas and such? Noonsite.com has a lot of info about other countries.
sailready.com also has a book about getting ready to cruise. I have not read it.
It is not too soon to learn radios, airmail, sailmail, marine radio and HAM. The Ham radio will take some time, not as much as before since you no longer need to learn MORSE code.
That's all I can come up with off the top of my head.
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