Yes, you can hurt your liver with Tylenol. In the cases close to me, and in the case described by the author, the culprit was clearly alcoholism.
Anecdotally, I've never heard a story about a man warned by his doctor to put down the Acetaminophen who kept going and died within a year.
Your comment about $500 worth of Tylenol seemed to diminish the role it could play in damaging the liver of even someone with no addiction. And $500 buys a huge amount of Tylenol.
The family member I lost (well-educated) was unaware of the alcohol/acetaminophen combination being potentially damaging. My reply here aims to inform anyone who may not be aware. Be careful.
This American Life has an episode that dives into the dangers. It's probably still one of the leading causes of overdose in the USA.