Hmm, on paper this sounds neat but I don't think that's how it works. Where the oil lives (the crankcase) isn't air tight. There's a breather valve https://en.wikipedia.org/wiki/Crankcase_ventilation_system which lets air and vapors out. While the engine is running, the vapors are directed back into the intake system so any unburned fuel in the vapors has a 2nd chance.

Either way, adding a little bit of pressure isn't going to make the oil come out that much faster. The reason why you might want to wait 15+ minutes is because if the car has just been running, oil is all over the place in all the nooks and crannies. Gravity is the only thing that can bring it all back down to the oil pan.

I do use compressed air when changing oil, but it's to run a vacuum extractor. Vacuum extractors make for a nice clean job, but they are much slower than pulling the drain plug.