This is only my second post on the forum so please go easy on me, but this is a topic of interest.
I have to say that (in my view) people make it too complicated. I have been smoking cigars for 25 years and one thing I have learned in that time is this - a cigar fresh from a box can often-times be the best cigar as an aged one or equally average/rubbish.
However, and more importantly, unless you are tasting two identical cigars side-by-side I would bet good money that we are not very good at distinguishing the variations in taste produced due to maturity - if it even occurs in the first place.
Again, in my view, there are so many external and internal variables to change how a cigar smokes that to try and suggest one can discern any changes would be a surprising thing to me. All of these factors will influence the taste/flavour and the perception of those very qualities - humidity, temperature, any foods/drinks consumed, mood, ambiance, activity etc. I just don't feel I could judge the same cigar from the same box years apart and make any genuine comparison. And if I did, it would be more my imagination.
Now all the above applies to me and I'm sure others like you all might be able to tell differences. I just enjoy the cigar, nothing more satisfying than opening the lid on my humidor, smelling a warm and moist cigar smell to give me a huge grin and hours of pleasure. But that's just me. Sorry for a long post.