I'm trying to create a character that is given an option after his death to choose the exact year he wants to be reborn in with all his memories still there. However, he is not allowed to let anyone know about his previous life when it happens.
Which year in the past would be best suited for that character to be reborn into to easily make a significant amount of money and live a carefree life using the memories from his past life? He is not allowed to create and invent things from the future, only take advantage of events he knows will happen.
One example I could think of is (around) year 1990, so by the time the character grows up he can invest in bitcoin and have it pay off later. However that is a bit boring for a story, are there any more interesting and clever occurrences from the past where a person that could have known about them would be able to take great advantage for his own good?