I think MSTR is clearly overpriced right now, but assuming a bitcoin bull market, it could easily hit new highs over the next year even if the premium over NAV were to totally evaporate. I think this premium is something like 127% currently, which would mean $160K USD bitcoin would erase the premium.
It's a bold gamble they're making - even if they're equally long bitcoin they could still end up losing. They're basically trying to time the disappearance of market irrationality in the middle of a bull market! I wouldn't be able to sleep at night.