Spot on.
My main concern at the moment is that if the gamble starts failing and he gets backed into a corner, his capacity to think "**** it".
Yeah, that's absolutely a concern. There's a reason why letting dictators go peacefully into exile has been a popular if entirely unsatisfying option in the past: fights to the death get really, really ugly. Your best-case becomes a palace coup and a post-mortem view of the sidewalk from a lamp post, your worst-case becomes something truly horrific. And that's when they don't have enormous nuclear arsenals.