I agree with Pat about the autocross - Boxsters can take an S4 (and a lot of other cars) in a cramped series of turns because sheer HP and torque are less important than handling there. However, if your friend's S4 is a full "Stage 3" and has coilovers etc. he will leave you behind on a track like Buttonwillow that has some decent straight sections.
My wife now drives my old B5 S4 and it's a great car in stock form but can be a real monster with some carefully chosen mods. It's much easier to get big power gains on turbo cars than NA ones.
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