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My wife and I lived on a 36′ ketch years ago, and have cruised extensively in Florida, Bahamas, Caribbean, San Bals Islands. It’s a wonderful way of life. It also requires a great deal of independence, self-reliance, resourcefulness, and resilience.
As another poster mentioned, sailboats are maintenance intensive machines requiring constant attention and periodic replacement of parts. In a post-collpase environment, parts and materials will likely become scarce and terribly expensive. A sailboat would be very difficult to defend in a SHTF environment. If things get bad in the states, they will be bad elsewhere. Out on the open waters, piracy will be a big concern as governments have fewer resoucres for preventing such things. In harbor, crime will likely be commonplace. How would you defend yourself against attacks of various sorts? Many land-based homes would be much, much easier to defend and maintain.
You can only carry so much in the way of food and water on a sailboat, so you’ll need to periodically go ashore to trade for goods. What will you use for money? How will you store and secure that on a boat? How will you keep from drawing attention to yourself when you present “money” for trade?
Of course, if you have a particulary marketable post-collapse skill (diesle mechanics and plumbers, for instance, will always be needed) you could do without money and, instead, work for whatever food/supplies you need. Having the ability to pull up your anchor and move to the next port (opportunity for work) is a benefit that land lubbers don’t enjoy.
Still, I would caution anyone not already committed to life afloat against pursuing that route as a way to deal with collapse. Find a quiet place on land where you can raise chickens and do some container gardening. If you are young enough, things will eventually settle down and perhaps then you could find a great deal on a small sailboat and use it for pleasure.
Collectable coins (and proofs fall into that category) are definitely a separate market; one that requires a good deal of knowledge and experience to succeed in trading. An IRA is not a hobby. IMHO, stick with plain old Krugerrands, Maple Leafs, or American Eagles. In fact, gold bars could be a less expensive alternative for an IRA (in terms of premium).