1) He uses his massive investment money (5k BTC) to gamble, making it nearly impossible for him to lose (he just keeps betting until he gets ahead)
I'm sorry, but this doesn't seem viable to me. He's just like any other gambler.
Have you followed him from the beginning (when he was Celeste)? To say that he is like any other gambler is like saying Michael Jordan is like any other basketball player.
I cannot see how a game of luck (JD) can be compared to a game of skill (basketball). Anyone has the same odds of winning, there is no skill in betting. Well you could argue that knowing when to stop would be a skill, but that has nothing to do with your chances of winning a particular bet.
People are just upset because large bettors do not come often and when they do, they have the potential to take a significant portion of the bankroll. If you are betting 50-300 per bet it is perfectly reasonable to walk away up 1500 or so from one session.
I remember back in the early days (before Celeste) people would argue about raising the max profit. Celeste came and won a lot of coin and then people wanted to lower the max profit.