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Is it "developed a system" so much as "continued taking the same one way bet"?
They aren't taking some new risk every time they buy more BTC. They just continually increase exposure, and this will seem like a good idea while prices are going up but a bad one if they don't sell before they go down again
Huh? Really?
I closed my eyes and ran across the road. Didn't die, crossed the road quicker than I've ever done before. Good decision!
Seems you're conflating good decisions with good outcomes.