I was thinking a bit more on this....  I own 2 modern cars, a Jaguar (:D) and a Lexus ( 

 ).  Both were purchased when 3 years old and off lease.
Combined, those two cost less than half of what they would have cost new, and even so in a year the Lexus has dropped another $5-6k and the Jaguar in 2 years has dropped another $5k.  Hmm, another reason to hate the unreliable Lexus more.... anyhow.
So I have been doing the math on the major project, my '62 PA Velox.  I have figured that to get the car where I want it, for it to be a regular use car over here, and we're talking drive it several times a week (Provided there's no salt on the roads as old Vauxhalls rust like nothing else) is going to cost me right around $25,000 maybe more.  I figure I'll have $3,500 in the drivetrain, $2,000 to add air conditioning, $3,500 in chrome, $9,000 in bodywork, and then there's all the other little stuff that adds up.  When all the dust settles I will have an immaculate PA with an all-Vauxhall drivetrain, 150hp at the rear wheels, no rocketship but performancewise likely at least equal to the average family saloon on the roads here these days (Camry, Accord, Malibu, etc).
I'll have a car that I can MAYBE sell, after thinking it over, for about $15,000 if I am lucky.  HOWEVER!  I won't have depreciation of a new car, if I spent $25,000 on a new Toyota Camry or  Chevy Malibu, I'll lose $10k easily in 3 years in depreciation if not more.  And while the Velox will be going up in value, the modern car will keep sinking.  My Jag listed at $67,000 new, I bought it 3 years old for $21,750.  Even if the original owner got it for $62k, that's still a shocking amount of money to lose on a car in 3 years.  I can't see losing $13,000 a year on a Mark 2 Jaguar.
So even if you do get a bit "upside down" when you compare it to new car depreciation... it's nothing.  
Or am I insane?