That is one thing Daniel Levy definitely isn't. I seriously doubt he has ever gambled a penny in his life. The guy is an accountant, born to balance books and haggle the price of something down to the bone. Gamblers come in two categories as you said, Winners and Losers. He would never take the risk of being the latter in any sort of financial deal. Call him lots of other things but a 'gambler' no, never.
As someone who works as financial analyst and whose hobby is watching football... I cannot disagree with you more.
From financial side, sure he keeps his books balanced.
But the gambling part comes in play in terms of impact of this on footballing side of things.
He is gambling quite often with how he chooses to strenghten the side or moving on players - buying players on last hours of deadline day that has been his operating method quite often IS risk in its essence. There is less time to negotiate and more things are out of your control than usual.
Plus we have seen for number of times how he decides to bluff instead of playing it safe while selling deadwood players. While he has been good with selling HG players such as Carroll, Prichard etc he has often failed with maximizing gain for overseas players (N'ije, N'Koudou, Janssen, Soldado etc). Many times he has overplayed his hand and as a result of that we have been stuck with paying wages to useless player who has no place in the squad and who is not trusted by the manager.