the absolute best thing you can do right now is just sample everything. When you smoke one you think you like, buy a single, and smoke it again, and then find out what it's made of and grab a few singles with similar blends, or post here what you liked about the stick and we can recommend you cigars with similar profiles.
Frankly, I would recommend that you don't buy anything but singles and fivers for the first couple years. For one thing, you might think "this is a great cigar" and then tomorrow smoke a very similar cigar that you like even more, and wouldn't you rather have a box of the latter? So don't be in a rush to buy a box of anything. I've been at this for years, and (apart from the boxes I bought for the births of my kids) I still only have maybe three or four full boxes. The rest are assorted fivers and singles.
My taste for beer has morphed as I age. Does a seasoned cigar smoker find as much variety in cigars as he does in beer or is that a bad analogy?
No, it's actually a great analogy. Like good beer, cigars are made from natural products and put through a refined process. Like beer, small batches can turn out slightly different from batch to batch. Like beer, there are a million nuances in flavor that can take something from light and mild to deep and dark and bold, and everywhere in-between. Like beer, your palate will slowly acclimate to what a cigar has to offer and after some time, you'll find you have a favorite. After more time, you might find yourself drifting from that favorite for something else as your palate develops. And like beer, the journey is the fun part!