I think you're perhaps being a bit too charitable. My sincere guess is that he's sitting on a considerable amount of bitcoin, and the im-so-broke is just a cover story to make recovery attempts sound unattractive. After all, that was his entire defence against investors considering (starting?) expensive legal action against him (along with threats that those would be the last to be "paid back").

We know he originally closed his site when he had secured enough money to basically comfortable retire. Then he only returned to the scene after seeing the ICO craze, and the opportunity to sell millions (!) of dollars of tokens to just reopen his site.

At one point even expressed interest in buying my site, I can't remember exactly but I think the number were were kicking around was ~10M dollars? And he was going to earmark funds for bankrolling it too. So I just don't see how the sudden leap from multi-millionaire with FU money, to penniless supposedly happened. I mean I wouldn't be terribly surprised if he developed a gambling problem or something, and blew everyone's money. But him trying to pretend he's penniless cause of "marketing" and "hacking" is ridiculous.

I could muster some empathy for him if he could be genuine for 30 seconds and try make amends. Until then, I think he's just an unrepentant scammer who is only here to add confusion and try clean up his name.