Extra-aging cigars does improve their taste
Case in point: About a month ago, I purchased a bundle of Dominican cigars with Connecticut wrappers. The price was irresistible, and I knew they were of good quality from a good factory, etc. So, I figured for everyday smokes they'd do the trick, and I placed them in my office humidor.
The next day, I lit-up one of the cigars to smoke with my morning coffee. To my surprise, it was not very flavorful at all and even somewhat bitter. I had had these cigars before with much more satisfying results. Next day, same thing. Day three, another blah cigar. At that point, I decided to let them sit and switched to something else. I also removed them from their cello wrappers, which is my normal practice, but I don't always do so with everyday cigars.
After just two weeks, the cigars had improved significantly in taste. It was probably a combination of two things: 1) The cigars needed the extra time to "settle." 2) By removing them from the cellos they had a chance to "marry" with the other cigars in the humidor.
Of course, sometimes you just get a bad box or bundle and there's nothing that will save them. I had faith in this particular blend, and all it took was some patience for them to pay-off. That said, had things gone the other way, I was happy I only paid $19.95 for the pack.
Moral of the story: Like the old "Chicken Soup" joke, extra aging may not help with some cigars, but it doesn't hurt. But from what I've tasted - and I think most other cigar smokers would agree - most of the time extra aging does improve a cigar's flavor.