I wonder if MSTR and MS ever do miscalculate this leveraged bet, I mean this is all debt marked against his company income, so I assume he must have contracts locked in with governments, no one could be this confident if they didn't have a customer who isn't agnostic to the economic climate.

Is he just making a bet that governments will always fund him at an increased rate + inflation will erode the debt his taking on and the diluting of equity?

Surely there is a breaking point where this strategy gets over it's ski's