[Joker_vD]

I definitely was not. "Courageous", "adventurous", "risk-taking", "reckless", "impudent", "bold", "daring", but with something that would mean "...almost and even to a fault or own peril", but without an inherent negative moral connotation is what I was looking for.

[MaxfordAndSons]

It doesn't have an inherent negative moral connotation when used amongst gamblers. It's been reclaimed, so to speak. But I suppose we're not amongst gamblers here, so, fair enough.