This kind of blew my mind when I realized that if you buy second hand and resell, you can own a product (often for years) for net zero dollars.
I was also delighted when I realized that instead of going through the hassle and cost of moving everything across the country, I could just sell it and buy roughly the same thing in the new place... again for net zero dollars! Teleportation!
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 read an article which described the free market as storage. People sell X when there is an oversupply and buy when there is an undersupply. The guy on the other end of those transactions acts as a storage provider.
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.
In many stores you can ask for "test skis". These would have been used for a few weeks as rentals and you usually get a significant discount from the normal retail 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.
This is what I recommend to people who are interested in a new expensive hobby. Try it before you buy it, make sure you love it and get an idea of what you like and plan your investment from there.
For tools, I buy the cheapest one. If (when) it fails, I replace it with one that is better along the metric that the original failed in.
For hobbies, they say "buy once, cry once", but there are so many ways to be unhappy! I won't limit myself! I say buy all, cry all, and learn all the different ways to cry. I don't ski, but for the analogy, I'd try short ones, long ones, cross country ones, racing ones, red ones, blue ones, etc and then only buy really nice ones once I understand exactly what the nice ones do that the others don't. There's a good chance that I'll learn I like skis more than I like skiing, and that's okay.