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When you rent the car and use your own insurance you are not insured totally. If you crash the car for any reason you are still liable for the time it takes to get the car fixed, just as if you are still renting it. In some cases that could cost a bunch. Or you can buy the extra insurance from the rental company, Expensive.
I would buy the two to three year old car, one that still has a warrenty, use my insurance and hope to get at least what I paid for it in six months or a year, depending on how good a dealer you are. Who knows, you might love the car and sell something else.
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