Another thing to consider is having 2 cars. By buying a second car that depreciates less (it's cheaper, older, etc.) you actually save money. And with 2 cars you can go no-compromise on both ends of the spectrum.
Recommendations: E39 M5, E60 M5, C5 Z06, 996 911 GT3 or TT, Ferrari F550. Second car: Honda Odyssey, Honda Accord