Maybe I should jump in here also. Like some others, I have done frame up restorations on a 53 MGTD (did the wood, also); restored a 66 MGB; and then a complete restoration on a 73 TR6 (every major body panel replaced). But I was spending more time working on the cars than enjoying them.
After that, I just wanted a car I could drive and that would be reliable. I bought a 91 Miata, with extensive upgrades to the engine, suspension, brakes, interior, etc. and have been driving that for the past three years (when my sons weren't using it ;-).
Now that my three sons have left home, and my wife and I have some more time to spend together, I've just bought a 99 IM for more than I ever would have expected to pay for a 'recreational' car. But, it's driveable on any highway, in almost all kinds of weather, and I hope it's going to be reliable. It's the most 'car' I have ever had, and frankly I still can't believe I bought it. In this case, I paid for work that someone else did, rather than doing it myself, and I guess I'm fortunate enough at this stage to be able to do that.
But, different stages in your life allow you to enjoy cars in different ways. And maybe certain cars are your way of 'rewarding' yourself for surviving to a certain age, after meeting all the obligations (good obligations) that raising a family calls for. I could have saved the money for my retirement years, but who knows what shape I will be in then, or if I will even make it that far.
A nice drive with the top down, and with your trusty right seater with you, is a simple, but not easily duplicated, joy.
I love the quote from 'The Sheltering Sky', and try to remember it often:
"Because we do not know when we will die, we get to thinking of life as an inexhaustible well, and yet everything happens only a certain number of times, and a very small number really. How many times will you remember a certain afternoon of your childhood, an afternoon that is so deeply a part of your life that you can't even conceive of your life without it? Perhaps four or five times? Perhaps not even that. How many times will you watch the full moon rise, perhaps twenty, and yet it all seems so limitless..."
My .04 worth, and apologies for the length of the message.
RJC