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Consider used Golf, Rabbit or GTI. Maybe a used CooperS. Lease returns are a good price bet. If RWD is mandatory, E36/E46.
Definitely get him to a car control clinic (BMWCCA or similar). If he's still a teenager, go with Tire Rack's Teen Survival Driving course. The skidpad & Slalom experience is very useful. Consider getting him into at least one autocross.
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