Owning one now, and also being in love with it, I'll advise that the Supra (the one I know best is the last gen "MKIV") is not for the faint of pocketbook unless you have the self-control of ...I can't even think of a mythical character with adequate self-control... to keep it stock or only slightly moded for more boost. But they're Toyotas and therefore seem to live virtually forever with normal maintenance.
Another car I've always liked and you can still find clean ones around is the Datsun 2000 or even the 1600. Recently there was one for sale around here, a clean stock car, for your target budget.
