for ~80k you can defiantly find a used 2007ish aston martin vantage w/ 10k miles... I know you said 2 years old, but the vantage is just pure sex on wheels...
997 would be hot... I personally dislike the boxster and cayman
the vette is a fun car too (i love my z06)... the grandsports are attractive, since they are available in convertible
How about a sportier sedan? Like the CTS-V, E63 and M5? Plenty of get up and go, with the plus of still being functional
I really think it comes down to personal taste... does he favor American? German? British? Italian? Swedish? Japanese?
Personally the Vantage is going to be the recommendation I take to him, or the old M6.
The problem is the custom modifications we're going to need to have done on the car.
Our driveway is on an incredibly steep gradient, so there are some restrictions as to how low and how long the car can be.
Otherwise we'll need to play around with the driveway or the suspension.