Glad to see him back!
As I recall, he timed things almost exactly right and did his major buy-in at around $2/BTC. I think he let this little tid-bit go, but could be remembering wrong. That he's back would indicate to me that he's back in buying mode. Whether he capitalized at 100x is unknown. I would not doubt it since his timing seems unusually good.
I doubt that, he's probably as close to a true bear as it can get.