I've been buying and smoking CCs steady for about 4 years now and I feel that in the past year, to year and a half I've "gotten a handle". I am by no means an expert, and never will be, but I do read sites like this one, try new CCs when I have the opportunity to, and have developed some good storage techniques thanks to sites like this one as well as other fine sites too. My early box purchases have aged beautifully, and over that time I've sampled regularly to experience the changes in flavor the cigar goes through. I can make reliable purchases on line, and get what I enjoy at a decent price.
For me this is pretty good, I never set out to be either an expert or collector, rather someone who likes to age and enjoy good cigars (regardless of country of origin). In this way it's taken about two and a half to three years to develop a handle on this hobby.
I think this this is the question asked in the OP, not expert or serious collector, just a guy who likes good cigars and wishes to have a good deal of knowledge in how to best enjoy and procure them.