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Might have missed some posts, but I'll assume insurance is part of his budget.
Does he go to a fancy high school in a rich area? When I was in HS, if you had something significantly nicer than those around you, it would get messed with. With that in mind, I'd vote for something under the radar a bit: Pre-2008 WRX or STI, 240sx, BRZ/GR86.
If showing up to school in a newish Merc or BMW isn't out of place: C5 vette, E36 M3, E92 335is.
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1960 356 Super 90 - EFI'd
1989 190e 2.6
1991 964
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