I think this comes under the heading of choose your own adventure. Start with familiarizing yourself with the two most basic base tobaccos that are the predominant leaf(s) in most blends, a basic Virginia or Virginia blend, and a basic burley or blend of burleys, so you'll know those in most all of the other blends you will smoke.
After that, it is a matter of selecting small quantities of many genres and blends, only trying small quantities even when you find ones you really like. Your tastes will always change over time. You'll learn to like ones you don't like at all at first, and get tired of some you love.
But maybe most important, don't go crazy and think you have to try every known blend in the world. Keep track of what you like, so you can size up blends from the specifications without ordering two ounces of everything in the world.
Enjoyment is the point whether you've been smoking a pipe for three days or fifty years. Slow down and enjoy it, and pay attention and study it enough so you make sense of what you are sampling. But enjoy, enjoy.Take your time.