I can tell you how much it costs and perhaps the math will work it's self out. Depending on your state's laws (garage & parking code) dealer ins for 15 vehicles worth aprox $30000 all together costs about $400 a month. Depending on the net worth of your toys it will change.
It may depend on the state the vehicle is registered in. In California, proof of insurance is required in order to register a vehicle, which is done when you purchase a car, and you need a license when purchasing auto insurance. I know in California that dealership wouldn't be able to transfer title to a person who doesn't have insurance since the DMV would require proof. Ask a dealership in your state for specific requirements.
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