Buy some 5 packs, and smoke them over the course of a couple of months. If you still like the cigar after smoking it 5 times, then get a box of it. If you're looking to buy in bulk, then I'd recommend some of the bigger samplers from CI or your website of choice that have some name brand, premium cigars in them. If you see Dark Shark, Hesitant Pirate, Ron Mexico, Raji's Untimely Demise in a sampler - avoid it like the plague. If you're not paying $2-3 a stick in a sampler, the cigars probably suck.

My first big cigar purchase was a Chosen One sampler from CI. It was a different one from two years ago, but I got 40 cigars for $100, plus a free 5 pack. I'm two years into seriously enjoying this hobby, and I've never bought more than 10 of the same cigar at a time.