I think the problem is too complicated (and too dangerous for mistake) to be done with calculations. I think it is done by trial and error, with lots of hard measurements. It should not be too difficult to determine when the plane is getting remotely close to instability.
National airport has a major crosswind problem with a strong wind out of the west. the alternate east west runway was disappeared about 40 years ago. It had been used by STOL commuter planes (Shorts I think) for nyc flights to take off and turn almost immediately to the north east.