re: When would you all recommend getting a new car?

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An acquaintance of mine, who I’ve known for about 10 years, does just the opposite. He trades vehicles every 2-3 years and buys a new vehicle.

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I see this too. Worst possible value for the buck.

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we can discuss his boat later

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Boats are just killers. Not just the tens of thousands (or hundreds of thousands) of purchase price. The costs of maintenance, docking, insurance, and repair are enormous.

I see way too many middle class or lower upper class people destroying themselves financially (without even realizing) with what is a luxury purchase. Renting a charter is probably the best option for the ten or fewer times a year that recreational boaters get out on the water.