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As far as insurance, yes you can be put on any car. Putting you on the '99 Sierra would be the cheapest option.
One question you should consider is if you are going to have the car in college. If you do plan to have a car in college, you might be better off with the Cobalt. That way the Camaro won't get beat up on a college campus. Trust me, it is very hard to keep a car from getting dinged up on campus.
Have your dad buy a 2SS LS3 for himself. Drive the Cobalt SS and make a deal with your parents that you will get the Camaro as your college graduation present. The Cobalt will be cheaper to maintain and you won't care if it has door dings all over it when you graduate. The Camaro can be kept nice for you by your dad and you'll have a great car when you get out of college in good shape.
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