He was an ivy league grad, vacations in Bali, and his family owns a country club and a chain of nursing homes. He almost certainly has more money than the guy he shot.
You think that a lone assailant had more money than the CEO of one of two branches of the 9th largest company in the world by revenue and largest health insurance company in the US? And if so, why wouldn’t he have hired a hitman with all that money instead? Or just paid for medical bills out of pocket? Or just had his own doctor that only served him and prescribed whatever he wanted?
He was CEO, not founder. The dude was only worth around $50 million. The shooters family owns a country club and an entire chain of nursing homes. They almost certainly have more money, probably a lot more money.
I can’t answer your other questions. Perhaps the answers will be in his manifesto.