As a newbee, I wouldn't jump right into English blends, particularly if you're going for that nostalgic smoke; that often comes from aromatic tobaccos. Pipe tobacco is a lot like wine in more ways than one. In terms of tastings, it's probably a good idea to become accustom to one genre before moving to another.
All of the advice about which tobaccos to get next are great, but the fact is it takes a long time to really understand the flavors of tobacco. When I first started up with the pipe, everything tasted like ash. That was due to poor technique as much as my being a novice. All the pipe videos in the world can't beat the process of trial and error. Use them as a guide, but know that you'll still get things wrong; however eventually, if you stick with it, you'll get things right.
Here is how the process worked for me:
Initially, I smoked a lot of aromatics. Slowly I was able to detect "something" going on. Next I moved to VaPers, which actually helped me understand aros better because I had something to compare. The thing is, I had to get my fill of aromatic tobaccos first. Then I went to English tobaccos; straight VAs after that; cigar blends after that. At first I was only able to discern the difference between blend "genres," but couldn't tell the difference between, say Frog Morton and Nightcap. I'm six years in and still learning the subtle nuances of tobacco flavors. I can really notice and appreciate the flavors of a good blend like Penzance, Stonehaven, Mac Baren's Vanilla Flake, Red VA Superb and so on. Finding these great tobaccos also helps me understand others because I'm developing a flavor profile, a set of reference points. All of this comes with time. It probably took me 100 smokes before I said, "wait a minute, I think something just happened..."