the more you do to a car, the less fun it becomes---the more it becomes a liability, and not fun to drive, since you're constantly worried about it:
breaking down
getting stolen
getting dinged
getting keyed
buy a performance car, and add minimal upgrades. my '05 GTO has about 375rwhp, has great manners, can be driven across the country tomorrow with the A/C blasting, and get 23-25mpg all day long on the highway. i have a catback/intake/shifter/dynotune. the wife can easily drive it. stock clutch is easy to apply. it doesn't draw attention from cops, vandals, etc. if the car gets a swirl mark, i don't care too much. its just plain fun to drive anywhere, with not a care in the world. i would recommend anyone in your position to try a car like i listed above--there are plenty of other examples of factory cars that are fun with minimal mods. the temptation is always there to do more, but you must resist it or you'll end up with another ball-and-chain for a car