This is very true. The most successful games of all times often have a consistent theme....emergent difficulty.
Chess is a great example. The rules of chess are pretty simple, you can teach someone to play in probably 10 minutes. But the game is so incredibly complex in play that modern AI designers look to it as a way to challenge themselves.
Chess is also incredibly boring.
I think that anyone who is trying to recapture a past gaming experience should try one very simple thing: play the game with the edition you think made it so special.
When you discover that it wasn't the edition itself that made the game special, but the people, the newness of the experience, your age, your surroundings, etc. then get back to me.