re: What are the ins/outs of buying a beach condo as an investment?

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And the often overlooked factor, for a family like mine that goes to the area anyway a few times/year,

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This is a big part of it imo. Find a location that is desirable and you can do find. Air B&B can be your friend. You also have to plan to get through the slow seasons as you may not rent it out at all. The non-affluent people I know that have done this tend to not plan for possibly having to notes at once without the extra income.