I was surprised how someone will plan with money he is not sure of.
I don't see how it was surprising. What do you want then? Just plan afterward? As you mentioned, he is a professional gambler and already achieved around 80% of his plan. Therefore, your friend was motivated and his approach to gambling is really good.
Maybe with those plans, your friend takes that as an inspiration to do his best, and fortunately, he's on the good track.
In my case, I'll just go with the flow with my gambling activity.