I don't meet the criteria set out by the OP. I have not had a chance this year to take trips more than a long weekend on the trails. However, I will say that as for "do I actually use my gear..." the honest answer is: most of it. And most of what is extra is intentionally kept as loaner gear.
A lot of the time I spend camping is one-night trips, taking people who have never been before (or who have never enjoyed it). I love introducing people to the outdoors, and for better or for worse, part of doing that is usually having the gear available to make it enjoyable for them If that means there are extra 2# sleeping bags on the shelf, then so be it.
People who have never been backpacking don't have the gear that would make it enjoyable -- 5# sleeping bags, Jansport daypacks and 6-person Coleman tents aren't meant to be carried up a mountain ... not even the little 3000-4000-footers we have here in VA.
As for me, I'm still well in the learning process as far as simplifying gear. Living in the city, I don't have a yard for testing gear, so all tests must be on the trail, so I look at a lot of our trips out as a chance for testing equipment and refining setups that I hope to use soon for longer trips.
My wife and I also have a gap in our fitness/comfort levels that we are working on. I'm comfortable with less ... and she is slowly moving that way (I'm proud of her), but when we met a little over three years ago, she had never slept in a tent before. So she's come a long way. We bought a tarp recently on the gear swap here, and are probably using Christmas as an excuse to buy bivies for one another.
As I've been simplifying, I've been doing what most people here do, and getting rid of extra/heavier gear. Three years ago, my only tent was a 9.5#, 4-person Kelty; that was replaced not long after by a pair of Mountain Hardwear 2-3 person tents in the 4-6# range when I found a good sale (need the extra space for taking friends).
Now we've got a Tarptent Double Rainbow, and are eventually hoping to have that and a tarp/bivy setup as our primary/secondary shelters. And so the camping shelf gets lighter and more functional over time... and gear either gets used or sold.