Re: Aspiring sailor searching for boats.
Before you buy a boat, I highly suggest taking a formal course and learn to sail. Be sure it is right for you and then you won't learn bad habits on your own. I've seen surprisingly good results from the week long, liveaboard intense course, where you get ASA certifications. They are also useful if you ever intend to charter.
Advising on what boat to buy is just too hard with limited information. Where will you sail? Do you want to be able to stay aboard for a night? Trailer it or stay at a slip/mooring. Auxiliary motor or no? The good news is, if you have $5 to $10k, there are countless options. The warning is, at those prices, you have to be very very careful and educated on what you buy. A single serious problem, like having to replace sails, standing rigging, wet cores or a diesel, could double the cost of the boat.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.