Scott is correct on this one. It's rare that you will ever recoupe money spent, and it's pure speculation, but that becomes a different debate.
A lot has to do with where you fall on the timeline. I have been driving since the spring of 74, and I have owned a total of 6 cars in my life, one of which I never registered and the other, and 2 of which became my current bird.
The motorhead syndrome has been around since cars were invented. Old school motorhead had yet seperated the 2 points of view of this thread. This is where I fall into the equasion. When I started out in the firebird, it wasn't a driver, it was transportation to work. There were a couple of folks that didn't fit the mold, but most of the motorheads didn't have a lot of money. When you popped the hood and broke out the wrenches, it had to fire up in the early am.
(Things have changed because there are now a lot of people who are involved with specail interest cars that--maybe they don't have money rolling out of their butts--are better off than many. Another thing that has changed since then is that a large part of the population cannot be labled as true motorheads because they don't do signifigant work on their cars. It's just the evolution of the interest in the cars, the changes that keep it alive.)
When I first bought the bird, there were still some who clinged to the wishes of being a soldier in the performance wars. It was a minority, and lots of the boardmembers on both ends of the 50 year old milemarker weren't warriors, or if they were, they retired from the battle. The ones who still played had a fairly good selection because supply was somewhat plentiful because demand wasn't such a strong force. And it started to die back even more as the timeline clicked.
I fall into the leftover group. It's been an obsession that will celebrate its 3rd decade in early September, and I manh of the bones in the bird have been titled to me since day one. So I cannot say eigher show or go because the car is an extension of me.