I can't pick one for each category.
For fun - FD RX7 with a built Vette plant and 6-speed or a Koenigsegg CCR.
For the weekend track car - Red M Coupe with an S54 and suspension work or a Noble M12 GTO.
For the daily driver - E39 M5 Touring, RS6 wagon, or a Subaru Legacy GT wagon with a built EZ30 and a GT35.
For the wife - Black Range Rover Sport on forged satin black 22's, or an SLK55 (hey, it's what she wants, right?).

(couldn't find black)
The showoff-mobile - Lincoln Continental 4-door 'vert, dark blue with cream interior and a satin billet wheel, on bags, or a 997 Turbo Cab (matter of time).
For Winter - 05/06 WRX STi with a GT30 and supporting mods, and blizzaks.