For fun - I'd keep my bugeye WRX, do an '06 interior conversion, and swing it back towards streetable.
For the weekend track car - Porsche 914, EG33 twin-turbo built motor, 6-speed Porsche tranny, widebody kit, with all the fixins.
For the daily driver - New BMW M5, bone stock.
For the husband/wife - FX45 with the appropriate bling.
The showoff-mobile - Aston Martin V12 Vanquish S, mildly modded.
For Winter - Legacy GT Wagon, w/ a JDM front-end conversion... damn that US bumper!