I'm only 20, so I'm not that far removed (although from the other end).
On the four seats--I'd almost suggest two seats. Less folks to distract you. A manual is a must for me, I'm a noticeably worse driver with an auto. Also, autocross and a BMW/Tirerack type drivers safety school. Let the biggest safety equipment be the driver, and equip him/her well.
My suggestions would be the following:
-BMW E30. Slow by todays standards, safe, later ones had airbags.
-BMW E36. Same as above, but probably safer.
-Crown Victoria. Should fit all your requirements except for the cool thing, depending on your definition of cool.
-Pick up truck. A full sized one for the safety issue.
-Nissan Maxima. Maybe not so cool, but a few minor details and it is.
-It sounds like you have, or at least know a miata, but I'll suggest it anyways.
-Subaru Impreza. An older one, obviously, to get into your price range.
-We looked around for a Ford T-bird. Always thought those were pretty cool, but I don't know much about them.
-Not easy to work on, but a SAAB. One of the safer ones out there.
BoxheadTim wrote:
W124 Mercedes? Very reliable if looked after and I think you should be able to find one within your budget. Late ones should have airbags.
Excellent suggestion, although maintained ones are few and far between around me.
there’s a lot of debate on this subject—about what kind of car handles best. Some say a front-engined car; some say a rear-engined car. I say a rented car.