It doesn't have to be an art, and the way to get it right quickly is to be slightly scientific. A five buck hygrometer is worth a year of intense experimentation.
Even then, there is a lot of experimentation in determining which blends you like at which moisture level, how tight you like to pack each blend, the ideal pipes for any given blend or genre, and every other detail you can possibly think of that might help or hinder the smoking of your pipe. All the little things can add up to create one of those seemingly magical smoking experiences where everything comes together perfectly, or maybe you packed the pipe a little too tightly or didn't dry your tobacco just quite enough and the experience is merely good but not great.
For me, after years of experimentation, the guidelines are pretty easy: Virginia blends dried almost crispy, latakia blends dried to where they are still pliable but if dried any further will start to get crispy, and aromatics are smoked as wet as the come from the manufacturer. Everything packed pretty loosely, with aromatics being packed just a little looser than anything else.