After owing close to a dozen used cars of various vintage throughout my youth, I decided to lease a new Vibe in 2004. It was a great car, and generally very practical. At the conclusion of the four year lease, I bought out the car and sold it, basically at what i considered to be a very fair price.
Since then, we bought a 2003 Nissan Maxima with the money (bought in 2008)... we were originally not planning on buying another car in teh family, but due to practical considerations, we realized that sharing a car was simply too inconvenient.
In any event, the 3.5L V6 in the Maxima makes it faster and more powerful. It also has every imaginable electronic gadget one would need.
However, it is by no means perfect. It is still an older car, which makes it suceptible to more frequent repairs. Though nothing major has gone wrong (knock on wood), the fact remains that the maintenance bits are getting more expensive...brakes, rotors, complete fluid change.
At the end of the day, the novelty of driving a "nicer" older vehicle is outweight by the peace of mind in owing a newer, most-likely more reliable compact. The fact that it is a larger vehicle generally means that everyday maintenance parts are more expensive too. Higher prices for tires were at teh forefront of my mind when shopping for snow tires.
In sum, it depends what your priorities are... but I would say that if your primary goal is a reliable A-to-B transportation tool, then a newer compact from a reputable marque (no silly Chevy-badged Daewoos) is probably a better bet.
On the other hand, if the thought of a 16 year old in a Civic cutting you off brings your blood pressure up, then maybe an older, faster car can be attractive.
