There are a lot of "You"s in your reply to my OP and I'm assuming those are addressed to the audience, not just me.I went through the first 10 pages or responses and you know what I found. Not one person who actually addressed this fine posters honest and sincere question; "what about that design speaks to you so strongly?" Not one.
Instead what did I see? Page after page of people singing the "praises" of 5e and 4e (forth edition is perhaps the singular WORST edition there is. There I said it to your face. It's horrible. It took the heart right out of the game by taking away even the trappings of injury from the game. A single night's rest makes everything better... just like a crappy CRPG. Go to an inn, rest a single night, and its all better. What a joke of a system.)
So I'm going to answer it. It might take a while, so buckle up.
Doyle wrote for Sherlock Holmes. “You have a grand gift for silence, Watson. It makes you quite invaluable as a companion.”
That right there is why.
For all the plentiful rules of later editions 3.x and later. For all the simplifications, for all the "untangling" of things and the changing of AC from a downward to an upward number. For all the pretty art in the new books. It lacks silence. Silence is the fecund earth in which our hobby grows, it's imagination.
Earlier versions are silent... on what your limits are, on how to tell you HOW to play the game. They give guidelines, they encourage you, and give you hints they're like the hand of your father hovering next to you after he'd taken the training wheels off your bike. The hand that is there to catch you if you need it, but which trusts you to learn to "fly" on your own.
In new editions you have to roll for intimidate, or investigate, or any of a number of things that in 1e or 2e you just DID. That you role played, not Roll played. In those older editions the rules were silent about how you'd intimidate that guard, or how you searched for treasure, so instead you sat at the table with your friends and you spun stories of how you did those things. You had to talk to the guard and the DM, being a fair minded adjudicator, asked himself, did their friend do enough to pull it off. You didn't have a roll tell you if some NPC lied to them, you relied on the DM's acting skills to carry it off and you became canny to it. You ROLE PLAYED. Sure AC might have been a little bass ackwards... but who gave a flip? That's easy to fix, flip the numbers around, it's 15 minutes of work and done. Tell me, does a table of numbers make that big a deal to you? Honestly? Are you going to claim for an instant that changing a mechanic from down to up made THAT big of an improvement? If so, you're a bald faced liar and you're being knowingly and deliberately obtuse.
So in short, why does the older version speak to me more than the new versions? Look at the prices that A copy of all 4 of the Wilderlands series are going for today. upwards of 900$ with maps in garbage shape, for that new cost 25$ total maybe. Go to a used book store and try to find an original DMG with the efreet cover and look at the price, if you find it for less than $200 you're lucky. People are cottoning in that pretty graphics don't matter. D&D is a game of the imagination, not pretty dice. And the earlier versions captured the essence of D&D better, by being silent when they needed to be. That silence is a quite invaluable companion to gamers, because it gives them more freedom and helps them confidently come up with their own ways of playing "let's pretend" where they don't need rules or dice rolls for everything.
About a month ago I had a discussion about modern art with a friend of mine. She has a Masters degree in fine art, and I am a simpleton who claims that I could do some of that art myself with a blindfold on.
One point she made to me was that in something like minimalist art oftentimes the void of the canvas is an important aspect of the art as a whole. This seems to me to be what you are saying.
To try to restate your point, but in a less condescending way, are you saying that to you older editions were the pinnacle of design because the areas of the canvas devoid of rules complements the core rules that are there?
I think that concept is a valid one, and can't argue with it. I would add, however, that despite 5e having a skill system, I think it has many less rules governing the system than 1e does. Do you feel that 5e takes up more of the blank canvas with it's ruleset than 1e does?