That's a very "Spherical cow in a vacuum" approach. You would need to accurately model the boss, as well as all your interactions with the boss up until your raise request, as well as the boss' environment when you make your request.

You could be on the wrong side of a reasonable boss, or in his good graces but during a bad day ...

That's the point the writer was making when he mentioned role playing games. In isolation, you could spend hours drafting the perfect plan, that wouldn't survive two minutes of contact with reality. You just don't know if your model is correct until you try.