This assumes your time is free. The used market has tons of friction.

I try to buy higher quality things, used if possible, and sell when I’m done with them. But this is primarily for ecological reasons. The complete cycle can be pretty annoying/time-consuming to the point that it’s probably economically a small loss.

Buy-side can take a lot of trawling FB/Craigslist to find an item that hasn’t been thrashed. Plus coordinating pickup time/location. This usually requires driving somewhere I wasn’t planning on going.

Sell-side you have to deal with all the flakes and ghosts, not to mention the people who will show up hours late. Giving away the thing instead seems to counterintuitively make the flake problem even worse.

Indeed, this is how it's supposed to work in an ideal world anyway. You only need to have some knowledge of the items and their tech to evaluate if they are useful second-hand or not for you. What parts wear and break and what are you able and willing to repair?

I have bought pretty much all my tools used. I usually buy low-tech solutions so my biggest concern most of the time is that the carbon brushes need to be replaced (and some models make this simple operation practically impossible, while in some models it takes under a minute). And I always look for dirty things that need a lot of cleaning since they usually go for cheap, and I'm cheap.

I've seen this described as using Craigslist/similar for long term storage.

Ski swaps are a great place for second hand or almost second hand. I’ve been to many where the local ski shops dump their old inventory. You get pretty much pristine gear for a fraction of the price.

You also get 'test bindings' that both toe and heel can be shifted forward/back to adjust to fit most boots. Disadvantage: weight. Advantage: adjustable.

On normal bindings the toe is often screwed in at one location to fit your boots and cannot be shifted later.