I've gone from small to large and back to small (tents). From being able to fit all the gear I owned in one backpack, to many duplicates of the same item, to trying to get rid of them. From rudimentary to super comfortable. These changes are about wanting to spend more time enjoying the surroundings and less time wrassling with gear. And also about a growing commitment to camping to the point of being willing to buy good quality.
A challenge is keeping the gear stock manageable when you do different kinds of camping. I do bike, kayak, and car camping plus backpacking. Bike and backpack are similar, but kayaking gear is different (more luxurious), so that's three different gear sets.
Aging has a lot to do with gear choices. In my twenties I biked around Europe with a 3/8" foam pad. Nowadays I can't sleep on anything less than a 4" air mattress. Cots start looking good as you get older.
Another switch has been synthetic to down sleeping bags. In the old days we had this fear that we were going to get our sleeping bags wet and die in the outback. Well, that never happened. I've only ever gotten my sleeping bag wet once and then only a bit of the foot. Plus now we have dridown and water repellent sleeping bags. I'll never go back to synthetic.
Since I started camping in the 1970s gear has improved tremendously. I don't appreciate unnecessary and expensive doodads, but on the whole mattresses, sleeping bags, tents, cots, chairs, backpacks, lanterns, and raincoats are much better than several decades ago. Bikes and kayaks too. So I think the whole outdoor experience has improved. Remember all those sleepless nights on the hard ground? Lugging backpacks that didn't fit, getting soaked in raincoats that weren't waterproof, warnings not to touch the side of the canvas tent in the rain. Not to mention vehicles that were old at 60,000 miles.