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I don't think you're being unrealistic. You should be able to find 1980's boats capable of cruising the Caribbean and serving as a short-term liveaboard for ~$50k. They may need updating, but I'm willing to bet you can find several that don't have major structural issues (or any structural issues) in your price range.
Maybe you should look at some boats in the 27'-32' range. For instance, how about a Shannon 28 or PSC 27?
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