If I was starting out, knowing what I know now, I would buy one Savinelli, one MM cob and one popular mom-exotic tobacco. I'd avoid aromatics, because they smell great, but they tend to be harder to smoke.
I made things way too difficult on myself. I was trying to learn to smoke with dozens of different tobaccos, all of which smoked differently. I wanted to spend money on tobacco, so I bought a succession of cheap pipes, all of which smoked differently. It took me six months before I could ever smoke without tongue bite, and another six months before I could smoke CONSISTENTLY without tongue bite.
Apparently, most people aren't as dumb as me, but it's got to be harder to learn 20 things than one or two.
Collecting dozens of different pipes, and sampling hundreds of tobaccos keeps pipe smoking fresh and exciting, but it's a hard way to learn the basics of "how to smoke a pipe."