Re: A bluewater live-aboard for under $20k
If I were in your shoes, I'd consider a different approach. Since you're new to sailing, and especially "big boat" sailing, why not focus on a boat that's "offshore" capable (not to start another war about what that means) rather than blue water, and one that is in good shape and comfortable? Get aboard a decent boat, make sure the lifestyle is right for you, and that you're really up to the task (I mean no insult by the comments, just that it may be a bigger lifestyle change than you expect). Depending on your career, you may find that the week or more that it may take you to get to the Bahamas (each way) may be more than you can really do more than once or twise a year. At which point, you'll want to assess whehter your goal is to sail YOUR boat into the wild blue yonder, or whether its more economically efficient for you to charter something.
As others have said, nobody is saying "don't do it"; heck there are several live-aboards and full-time cruisers here. Just trying to make sure you're making a fully informed decision before investing time and money into something that might bring you less happiness than you envision.
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