Why the Maranello?  Depending on your experience, I would lean towards a
328 or 355.  Thus you would get in the game with perfectly drivable
wheels and, while not the full purist 12 cyl Ferrari effect, certainly a
good time.

When I was at your decision point, I bought a 1967 330 GTC, which was
great fun, but I couldn't park it anywhere without drawing a crowd.
After about a year, I traded it for a 1962 250GT SWB California Spyder.
 Yes people, time has shown me to be an idiot.  I sold the California
in 1974.

Were I to get back in the game, I'd lean towards a 550 Maranello myself,
not knowing any better.  A few years old; values are down; quite a
rocket, relative to mortal vehicles.  However, I haven't driven one yet
and have no idea about creature features, although I hear the paddle
shift is a wonderful thing and lets one enjoy driving without the
traditional heavy clutch.

All right everyone, throw your polo mallets...

MrNutmeg