I think it's simply a matter of immersion and then refinement. You start off diving in and trying all kinds of pipes and tobaccos, and then finally you find yourself. You end up with the pipes that smoke best for you and fit your view of yourself, and the tobaccos that continue to satisfy you. Myself, I've certainly bought well over a hundred pipes and now have a couple dozen, and the tobaccos I've tried I couldn't begin to count but now smoke less than a dozen regularly. My actual core, what you'll likely see me smoking daily, is maybe half a dozen Stanwells and a 3 or 4 Petes, and a few burly tobaccos, a couple of Lakelands.
When I started out in this hobby almost a decade ago I couldn't really understand why so many old codgers were happy with 3 or 4 simple inexpensive pipes and 1 or 2 simple burly blends. Figured they just didn't care about the art of pipes and the array of flavors available in high end tobaccos. Wrong. Though these things are great, there's also beauty in simplicity. A lot of old dudes had it figured out.
No, I don't try too many tobaccos anymore. I've already tried so many.... Still have dozens of little jars stashed away. I've found that my own personal circumstances prohibit me from being a collector of pipe art, so I collect the best, most interesting, good inexpensive little smokers I can. I've owned pipes by Bang, Hedegaard, Chonowitsch, Castello, Dunhill, Barling, Sasieni, and on and on and on...... I kept very few of those, mostly a small handfull of Castellos, but for the most part I am quite happy with the 10 Stanwells and the 10 Petersons I own. There are a few other odds and ends, a lone Ashton that's simply too good to let go of, a couple of pipes carved by or given by friends, etc., but for the most part I just decided to be happy with culling down to the best smoking Stanwell and Peterson pipes I could find, and enjoy them. Same with tobacco. I could be happy with 2 or 3 burleys and a couple of Lakelands, and that's it.
If someone said "You're going away for years. Grab one pipe for each day of the week and take 2 tobaccos" I could do that now. Not so long ago I couldn't have.