You solve this problem by acquiring an equally pleasing toy to have fun with in the present. I love my bikes but eventually I plan on getting rid of all of them to good homes so no one has a bunch of shit to sort out after I am dead.
I have been lucky enough to own and ride dozen's of classics and to have been born into a motorcycling environment. If I kept all the shit my father and I ever had we would have to be rich enough to build a museum or warehouse.
As long as you send them to a good home there should be no regrets, must like marrying off a daughter to a prince.
By the way when I was a kid I used to ride a Gilera like that around the neighborhood and through the woods etc., it was the first "real" motorcycle I got to ride a lot, it is still sitting in my old man's barn. It seemed huge when I was a child trying to ride it, but now it seems tiny when I go look at it. I think it has 17" wheels.