Re: New guy with dumb questions.
There are no dumb questions.
The answer to both of your questions is, "It depends."
In fact the answer to most sailing questions is, "It depends."
Some old boats are waterlogged pieces of flotsam- sailboats have some unique issues that power boats don't have like lots of opening sin the deck for water to leak in- around chainplates, mast, etc. which can cause a deck to get waterlogged, the mast step to rot out , etc. Having said that, the vast majority of sailboats in North America are more than 25 years old and are actively used.
Can you go to the top of the mast on a Cat 27? How big are you, how strong are the halyards, how strong is your winchman? Yes, it's possible for the right person... but check your equipment carefully and have a safety line. The only thing worse than having to go up the mast is only going most of the way up the mast.
It's 5 o'clock somewhere:
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