I haven't experienced this, but I would guess yes. Wine and beer both have peaks in their aging. After this peak is reached, the quality deteriorates. Being that these are natural products and cigars are natural products this would make sense. I have read posts on CS regarding cigars losing flavors or becoming bland with age. I'm sure someone with experience will chime in....I hope so because this is just my guess.
Completely different chemical processes. Wine requires a preservative agent to properly age, and acidity is pretty much it. But as wine ages, fruit component diminishes and drops out (in the form of sediment along with tannins and other solids) while acidity stays at a pretty much constant level. Alcohol is also a preservative, although not as important one as acidity. But you're right, of course, that wine can only go on for so long.
Beer has almost no preservatives to keep it "fresh" and thus spoils much faster.
With tobacco, strength is determined by the amount of nicotine, right? And since this is a "solid" product, not based on liquid, I am not aware of a chemical process that diminishes nicotine amount with age. Sure, as cigars age, they loose ammonia and other compounds present in freshly rolled cigars, and similar to wine, start developing more flavor and complexity. Similar to young wine, where tannins are still present, the mouth feel itself is what gives the palate an impression that wine is "bigger", while all a palate feels is the physical impact tannins have while coming in contact. Flavor is there but is dominated by tannins (abrasiveness), strength is also there as represented by fruit component, acidity and alcohol.
Same with cigars, young cigars simply present themselves differently than aged ones. Nicotine is still there. And in deference to wine, cigar is a solid product and thus, can age and stay in good shape for who knows how long. I have not heard of a cigar "going bad" with age, but of course I am talking about quality cigars that are stored in good environment.
Whether one likes cigars young or with some age on them is a matter of preference, as with any other product. I like them with more subtlety and complexity, same as wine. Even though I smoke them young to evaluate if I should buy more or not, I then tend to buy a good quantity and let them sleep and develop more (same as with wine).
As with wine, though, one must start with quality grown, fermented and processed tobacco, otherwise aging won't do much save for expunging ammonia and a few other compounds with time. So, while one would be advised to age a quality stick, there is not much sense to age cigars meant for early consumption (cheap bundles).
On the strength issue, and I see claims that cigars loose strength as they age, I do not agree. Just smoked a
35 year old RyJ Petite Corona over the 4th of July and while it showed tremendous complexity, the strength was there in spades and on similar level as fresh ones. Sadly, that was my last one.
I also have a bunch of
12-14 year cigars, CC, Nicaragua and Honduras grown, and they all show same levels of strength as fresh ones.
Thus far, my own experience contradicts a number of statements made on CS and so far I have not seen one scientific explanation in support of these claims. Or any explanation, for that matter.
I know the chemical reactions/processes that eventually let wine spoil, but so far I am not aware of ANY such process that will lead to a cigar to go bad. Is it myth? I think so, but if anyone has information to the contrary I certainly would love to hear/see it.