Join the noob pib, great trade thread to learn a bunch of noob cigars.
I never really progressed very far beyond the "noob cigars" because I'm a cheapass. But there are TONS of excellent smokes at $3/ea (and some under) and even more at the $5 point. Stick to cheap decent cigars, acclimate to proper smoking conditions and go from there. Buy samplers, but not the cheap ones.. Well.. some of the cheap ones. Avoid cheap Gurkhas. Avoid Gurkhas period. Don't think that because a cigar is $$$$ it's great, especially if you're just starting out, you're not going to be able to discern what makes that cigar so pricey.
There's a lot of experimentation and trial and error until you figure out what works for you and your environment. Where I live, it's extremely humid from May through September and I need to smoke my cigars dry from the box due to ambient humidity. So I keep a "dry box" which is just a cheap leaky humidor with a couple 65% Bovedas that keep it around 62%. The colder months are of course much drier, and I can smoke straight from the humidor without a two week dry time. This took me about a year to sort out.
Your tastes will change. Personally, I started cigars with ACIDs. I quit cigarettes in '07 but picked up an ACID cigar in 2011 when I found out a local shpo was owned by a guy I knew through a local gun forum. I stopped in to meet/chat with him and smoked a cigar. I enjoyed it very much. Over the next two years I bought mostly ACID cigars, maybe 5-6 a year. Went to an event at the shpo for La Gloria Cubana and smoked two cigars that night. Don't remember what they were, but I do remember being unimpressed, especially after spending $25 on them. But then I started looking at cigar reviews, cigar forums and the like and trying to learn how to taste and enjoy a proper cigar. I pretty much stopped buying infused cigars at that point and started exploring different cigars.
I made the common mistake of buying large quantities early on. Luckily these were mostly large samplers and from them, I found a handful of smokes I enjoyed. But, another year later, many of those that I really liked, I no longer have any interest in smoking. Personally, I moved from an early obsession with full flavor full strength cigars to a preference for mild/mild or mild/medium. There's probably 100 cigars in my humidors that I'll never smoke myself, but keep to trade/give away.
Start with excessive storage if you really think you're going to get into this. I started with tupperdors. I had two large ones, about 50 cigar total capacity and quickly filled them. Would honestly be enough if I wasn't the type of person to jump in head first into any new interest/hobby. I built two "hybrid humidors" which are watertight shipping cases with Spanish cedar boxes built internally, along with two cheapass Chinese humidors and one quality desktop humidor and I'm a little more than halfway full.
Bovedas or Heartfelt beads only. Ignore everything else. /story
Overall, It's a whole world to explore, get started and we'll help you along the way.