If he didn’t misspend the wealth in his first-age, he will become the wealthiest merchant.
If he ordained in his first-age, he will become an arahant.
If he didn’t misspend the wealth in his middle-age, he will become the second wealthiest merchant.
If he ordained in his middle-age, he will become an anagami.
If he didn’t misspend the wealth in his latter-age, he will become the third wealthiest merchant.
If he ordained in his latter-age, he will become a sakadagami.
I think we have free will. However, past habits in past lives may make certain choices more likely. For example, if someone has ordained as a Bhikkhu in one of his past lives, it might make it more likely for him to ordain in this life too, but it is still dependent on his choice in the present, but the chances of him ordaining would be very high because of past kamma.
I also think even Venerable Devadatta wasn’t “destined” to do the things that he did. However, because he had done bad things to the Bodhisatta in previous lives, it made it more likely for him to do bad things to the Buddha in the present too, but if Venerable Devadatta was able to restrain himself in the present, he could’ve avoided committing bad deeds.
So, I think we have free will but our choices and actions may be influenced and conditioned by past actions from past lives.