The lottery’s a dream for guys like me. This guy was already living his dream. He’s already won the lottery.
I imagine he is already living comfortably. I seriously doubt that he can drive all those cars, and maybe he should part with many of them on that basis. But having that collection is his dream, and there is nothing wrong with living his dream.
I see no reason he should part with any of them unless he himself feels like it.
Unless, of course, he’d like to give one to me! 
It seems to be popular reasoning that if your not driving a car you should sell it to the next guy. Many past friends/acquaintance have told me they offered someone $500 for a car and the offer was rejected. They were upset because the owner doesn’t drive the car “it just sits in the back yard”.
If my garage door is open people will stop and offer me up to $10,000 for an old Dodge in my garage, I don’t tell them there are two more in the back yard because I want them to leave. They will carry on about how many old cars they owned over the years and somehow their selling their favorite cars on a whim means that I should sell them my car. Dream on.
MikeInNH: Yes! He keeps them because he loves them much more than he loves money. I’m the same way. Money is variable. In ten years it could be worth nothing.
Money is totally without value if you already have security and don’t use it for something you enjoy. You can’t eat it, it can’t transport you anywhere, you can’t bath with it… once you’re beyond security its only value is to do or get things you enjoy. This guy has his priorities right.
There’s more at stake here. I doubt if Lenny really knows what all these cars are worth or CARES!. He’s a nice old guy who is basically stuck in a pleasant rut, and he will not likely get out of it unless he loses his health.
As stated, I hope the relatives know the value of his possessions and dispose of them properly when Lenny is no longer able to take care of them.
I grew up in a rural area and numerous old farmers stayed on their farms long after they could no longer maintain them as a viable business. They did not want to be uprooted.
My dad sold out and bought a house in town and spent time travelling. I think he was an exception.
I doubt if Lenny really knows what all these cars are worth or CARES!
I’ll bet you he knows exactly what it’s worth. But there’s more to life then monetary value. For some people it’s all about the money.
I’m jealous.