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How old it too old when it comes to sailboats – I have my eye on a few that are well over 15 years old
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I have shoes older than that. Just as with shoes - it's the condition not the miles.
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What would be an optimum size for a couple to live aboard – with room for guests… 50ft?
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Depends on the guests. I suppose it also depends on the couple too. Most people I've found are no different when on a boat. Guests don't care as much where they are if they are happy to be there. It never really helps to get a boat based on guests. THe bottom line is you'll never have that many to matter. You need room and
displacement to carry all the stuff you bring. After that it's just too much boat. They need a lot of
work.
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What would be your ideal boat for cruising the East coast, Bahamas and Caribbean for a few years.
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I'm thinking you could be happy with the budget you have in mind. I don't know you so it's only just a guess. I'm pretty happy in that budget. You could go other places too. I don't see that as a limitation.
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I have always been a firm believer in buying the best quality you can afford – I would prefer an “older” vessel in Bristol condition to a newer production model with lesser design and craftsmanship…
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I'm more of a - more design person. Older is fine but poorly designd just does not get better with age. Older boats tend to show the difference more. Being newer has an advantage if it really is ugly. It's the first thing that comes up - "nice new boat".
Boats are clearly more about you than someone else. You need to find the ideals that define the best one for you. Too many boats!
Spend some time and look around here. There is just so many details to
work out. You could find some good ideas here.