It is funny about that '67 Camaro because it would be worth more if he had done an all original restoration than spending ultra big bucks on "bastardizing" it. No Camaro enthusiast will ever touch that car. But like you said, hey, if that's how he wants to spend his money then go for it. I've got about 18k "invested" in a Jeep that will never be worth more than 7k. But I have had at least 10k worth of fun with it so I am still coming out ahead. (by my reckoning, you have to justify it somehow.) At least I know where my money is going and why. When I look at Jeep modifications I say "This part costs $1,000, will it give me $1,000 worth of enjoyment?" Take the ignition upgrade I am doing to the Ferrari. Will the $500 spent make the car worth $500 more? Maybe, maybe not. Will I get $500 worth of enjoyment out of it? Yes!
And, no, I will never be ashamed of what I have. Like you, I work hard for my money and buy things that please me. When I was a kid I built a model of a 308 and dreamed about having a car like that. Then Thomas Magnum had my car! Now I have one too! I am estatic!