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It sure seems to me that you have been diligent in correcting problems and even trying to anticipate the unexpected. I can't see any reason the boat shouldn't be sailed outside. Weather permitting of course. If you trust your captain, let him decide. As to the boat not having seen anything but calm water for a long time, what the heck does that have to do with anything.
You are not talking about an Atlantic crossing or anything here. Some glitches are sure to surface but so what. Go for it.
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