Personally, I think you should find some samplers to try as wide a variety as possible to find out what your likes and dislikes are. If you can find five packs of cigars, you can get a good idea of what may appeal to you. It's never good to make a judgement about a brand or vitola based on one or two cigars. I would stay away from buying boxes at this point. I jumped in buying boxes and wound up selling alot of them off. Oddly enough, as my pallete developed, I found some of the cigars that I sold off I enjoyed later. The cigars needed time to develop also!
I'll send you a sampler of some smaller cigars that will give you a place to start. I don't happen to be a fan of the Quintero's etc., but there are some good machine made cigars out there. Some of the RyJ machine made and Upmann's also are pretty good actually. And I like the Fonseca #1 for a change of pace.