alt Hacker NewsYes, it's entirely possible he may loved every minute!
I don't know if the fact he's financially successful affects my read though. It's certainly obvious he had money but unfortunately I don't think the money precludes an unhealthy obsession. Infact it might make it worse.
Unhealthy in what way? The article mentions that he is (or was) an active seller as well as a buyer. His lifestyle doesn't seem particularly unhealthy either.