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Originally Posted by MAXUM
Good point on the equity piece, 20% down is the bare minimum for a second home as a general rule, they can get even more needy if it's seasonal or if the value of the house is out of the value percentage skew versus the value of the land. In other words if the value of the building is to little of the overall land and building package price that can set off red flags.
If it were me I would worry about securing the property first and worry about buying a boat and improvements later. In fact your friend may find out quickly that spending big bucks on an island boat isn't necessarily a good idea. Whatever boat he/she gets will inevitably be used not just for pleasure but also as a freight/trash hauler. Not necessarily something you'd want to do with a 50K boat. Plus having two boats is really ideal, when one breaks you have an alternative way off the island.
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Thanks for the feedback. Especially about the boats. Would perhaps a used 15 foot Boston whaler and a 22-24 pontoon be a good combo? I know a lot is personally preference...