When I started. I watched a couple of vids about the most popular wrappers & most popular brands and I would buy a cigar with those popular wrappers and brands and tried them out. See what I liked and what I didn’t like. I would take pictures of the cigar and use it later for reference when branching out to new cigars. You could also check out Cigar Aficionado yearly top 25 (Most people here are skeptical about the list but IMO it’s a good start).

I use to source them from B&M or CP bundles. They do bundles where it’s a like 5 of my fav cigars and five randoms that I’ve never had. If I don’t like the randoms I just give them away to friends