It seems to me that the scenario described is more a matter of whether or not the airplane is left with sufficient control power to continue with safe flight and landing, not a matter of pilot ability to handle airplane path control.
The OP pilot suggested this was an recurrency training exercise not a test flight. It seems there might be 3 box ticking exercises being combined into one scenario. Now how can we tick off a 'flight control' & 'x-wind' landing' & an 'out of trim landing' all in one? Good game. It might be a confidence boost if you survive or a total confidence cruncher if you don't. And what does the erstwhile instructor do if you go off the edge? Will it be a debrief & demo then more training to achieve said goal, or is it a S- in the training file and move on to the next box? And given that there might be little time for that what will he do if you decide, correctly to GA. Will there be time for the correct diversion to a more sane place?