1) You can estimate the likeliness of DDmax right at start as roughly (0.5 * length of DDMax) / (Simulation time).

2) Hard to answer - there is no simple formula.

3) This is almost certain. No matter how profitable a strategy is, at some day there will be a drawdown that exceeds the DDmax of the simulation.

4) When I think about it, yes, this could make sense, maybe as another flag in the .ini file. But the phantom flag is a better method, as it stops losing components much earlier.