I like to approach palate development for cigars the way we do for wine or beer. The first time one tastes wine, regardless of color, grape terroir or vintage, it tastes like wine. The same goes for beer. As we are exposed to more of each, one can develop a preference for red vs. white or a light beer vs. a dark beer. And further exploration allows consumers to begin to prefer Cabernet Sauvignon over Merlot, or Italy over France.... Or, ale over lager, for example.
The same development occurs for premium cigar enthusiasts. The first few times you taste a cigar, or smell a cigar.... It simply tastes and smells like a cigar, no matter the origin of tobacco or brand. However, the more one pays attention to what they select, the more they're able to "split hairs", and differentiate one cigar from another, preferring Dominican or Nicaraguan made cigars, "dark" wrappers over lighter colored wrappers... fat cigars or thinner cigars. And while of course it's not a perfect science and there are exceptions to every rule, it at least begins to lay a foundation of assumptions that permits the enthusiast to make educated guesses about a cigar prior to trying it.
Then the real key is to keep track of the ones you like and the ones you don't. And equally important is to record the reasons why you liked one or disliked another, in whatever vocabulary or vernacular you have. You don't need to record "herbaceous finish with a spicy mid palate impact and notes of anise" (though you certainly may... if you're able to detect such complex flavors). But, was it hot or cool? Did it dry your mouth? Did it taste good or bad. And were there any familiar flavors that reminded you of anything you've had before? "This cigar reminded me of the way my morning coffee tastes." "The aroma of this cigar smelled like the aroma of a bakery." From there, you're able to begin to draw conclusions by comparing the things you like, with their details and components like the tobaccos used, the country of origin, manufacturer, size etc...
Finally, shop with a retailer that has a great a great staff, a great selection, and a great point of sale system. That way they can not only keep track of what you purchase, but can also make sound recommendations based on your experiences. For you cigars are a hobby. For us, we've made our hobby our profession. And it's truly our pleasure to help guide you on this journey.