My advice may seem a bit unorthodox but please indulge me for a moment. It is often said that to properly enjoy a Porsche, one must drive a Volkswagen first. That being said, I would suggest that you start out with a light Burley-based blend that is easy to smoke, kind to the palette, pleasant to the senses and light on the wallet.
Those first few months of pipe smoking is usually spent learning to actually smoke the pipe, fill the pipe, clean the pipe, etc. Once you are comfortable with the pipe you will begin to start noticing the true flavors of tobacco. The subtle nuances of each type of leaf will reveal themselves over time, gradually maturing the palette to a much higher level of sophistication. As you learn to smoke proper, you will learn to taste tobacco proper.
As you become more seasoned, your desire to explore more flavors will take you on an adventure where there are thousands of quality blends available. If you have started out with a subtle gentle blend you will be rewarded with the ability to appreciate and understand what a fine premium quality blend can be. I started out with Captain Black Gold for my first year then moved on to various "drug store" blends. My first real high quality blend was McClelland Virginia No. 25. I continued on to other high end tobaccos and have never looked back. I would never had appreciated the "good" blends had I not experienced the lower-end lines first.
I would recommend these blends as great starters: J.M. Boswell's "Premium Burley", "Magnum Blend" and "Northwoods". Mac Baren's "Burley London Blend", "Golden Extra" and "Original Choice". Even good old "Prince Albert" is a good inexpensive blend.
So cut your teeth on the basics and save your money then enjoy the luxuries with your new tobacco-tasting abilities!