I'm thinking single sig with a string passphrase is the optimal option for someone doing it themselves but wants to keep it simple to recover by spouse etc.
When you're used to parabolic bull runs and they stop, it would be a bit of a shock. But failing to understand why and thinking it is somehow bearish is doing themselves a disservice.
The power is not in his hands at all. MSTR and it's Bitcoin are a regulated entity owned by the shareholders. Even if 4% of the supply was owned by an individual, how is that a risk? The worst that can happen is that it was sold all at once and the price dipped briefly. Big whoop.