I agree wholeheartedly, the pre-Win95 world was exactly what you've described. At that point, the average Mac owner employed 7 or 8 apps to the Windows user's 2 or 3. I don't remember the exact numbers, but they were the product of solid market research. The Mac WAS the natural platform for small shop and garage level creativity back then and is again right now. Altsys Fontographer -> Aldus Freehand was the work of a couple of the members of NYMUG who hit it big. MYST came out of a garage and almost every small productivity app came out for the Mac first, it was a sad day when the tables turned and we had to hope for a Mac version to be brought out froma Windows development.
Today is as exciting as yesteryear in many ways, but revolutionary changes to entire industries were made at the turn of that decade a score of years ago. I miss that. As for the idiocy in the infinite loopiness, that's the stuff of legend and playing what-if is a natural for the collectors of ancient computers, cameras, firearms etc.
Heck, , the InterNet worked just fine, but the Navigator's development in the timeframe of the nostalgia you're belittling(maybe too strong a word) changed the face of the World with its Wide ranging Web of connectivity. But I'm beginning to become nostalgic about the day when you could actually see, hold and try a product in a brick & mortar establishment that employed knowledgeable people.