4. What is his father like?
There’s two extremes to this: A man can be an exact clone of his father or he can learn from his father’s flaws and try to better himself. See if any of his father’s traits (good or bad) are part of his makeup.
If his father was a bum or loved to gamble, that doesn’t exactly mean he will, too, but it’s always a good idea to be super aware of his characteristics and mannerisms. If any negative aspects that resemble his father start to blossom, it may be a sign that there’s more to come.