Being an owner of a '67 Impala, a '71 Roadrunner, a '69 Roadrunner, a '69 gmc pickup, and a '72 Mercedes 280, at different times, I can say with certianty that its about the fixing as well as the looks.
None save the Mercedes were even CLOSE to original, all were fixed up in my garage, all had engine transplants (save that 280 again) and they were all more FUN to drive and fix than the Mercedes.
Now if I were out to impress the hoodlums, the Impala was the best, the gearheads loved the Roadrunners (never mind how bad they actually were) but the ladies? yeah you guessed it, the Mercedes always seemed to be a hit.
Now lets do some quick and dirty math. the mercedes was serviced professionally, oil changes, tuneups, brakes, suspension, transmission services and professional detailing = A HELLUVA lot of money every year.
A '67 impala that never saw a shop, had a 454 shoehorned into it in a barn, was painted with the cheapest duplicolor paint I could get in bulk, smoked tires all day long, was comfortable, rolled like a boat, and finally ended its life by stopping (typically) 50 feet over where I needed it to.
Personally gentleman, its all about the ladies, I'm stuck on my mercedes kick for obvious reasons, I doubt I'll ever build another "muscle car," but had I improved my braking capabilities with the impala, I'd probably still be driving that.
I don't honestly think it's the money, or the car, or even the opinions of others, its what makes the DRIVER/OWNER happy. Some find happiness in getting all the gearhead's attention, some like the car but want better,and some like all the phone numbers they get from the ladies.
Me? I'll be cruising the strip in the mercedes and calling up the ladies for an evening on the town