Senior White was a lucky guy, so he didn't suffer from decision paralysis - as long as external influences didn't sway him, he tended to make choices that leaned towards the "best" direction.
Even when faced with crucial decisions, Senior White could resort to methods like flipping a coin to happily make choices that were most advantageous to him.
Because Senior White's luck only favored him personally...well, while he was a mobile source of luck, hitching a ride on his luck always came with a bit of risk.
Senior White's luck only applied to him personally. His personal luck didn't mean those around him would share in it. In fact, it was quite possible that those around him would endure some hardships, with Senior White reaping the benefits.