You are standing in front of a listing, or a showroom, or a secondhand app, trying to work out whether the lower price is a good deal or a problem waiting to...

You are standing in front of a listing, or a showroom, or a secondhand app, trying to work out whether the lower price is a good deal or a problem waiting to happen. The honest answer is that it depends on what you are buying, not on some general virtue of buying used. A few questions applied consistently will get you to the right call faster than gut feeling will.
Before you look at a single listing, run the item through three questions. They matter more than the price tag in front of you.
Where is it on the depreciation curve? Some things lose most of their value in the first year or two and then level off. A car is the clearest example: the steepest drop happens early, so a two or three year old model can cost noticeably less than new while having most of its useful life still ahead of it. Furniture and hand tools behave similarly. Other things do not depreciate the same way at all. A mattress does not get cheaper to buy used because it is not really the same product once someone has slept on it for years; the part you are paying for is support and hygiene, and both degrade with use rather than sitting flat.
What is the warranty actually worth to you? A warranty is not a nice-to-have, it is insurance against a specific kind of bad luck: the unit that fails early through no fault of yours. On something with expensive, hard-to-diagnose failure modes (a washing machine, a laptop, a car's transmission) that insurance has real value, and buying used usually means buying without it or with a much shorter version of it. On something with cheap, obvious failure modes (a hand saw, a bookshelf, a stroller frame) the warranty was never doing much work, so losing it costs you little.
What does failure actually cost you? Not the replacement cost. The cost of the thing failing at the worst possible time. A used power drill that dies mid-project costs you a trip to the shop. A used car seat that fails in a crash costs you something you cannot buy back. Rank what you are buying by how bad the worst case is, not by how likely it feels, because low-probability high-consequence failures are exactly the ones people underweight when a good price is sitting in front of them.
Once you run items through those three questions, a pattern shows up. Used tends to win when depreciation is steep, warranty value is low, and the cost of failure is recoverable.
The pattern reverses for a specific set of categories, and the reversal is not about being cautious for its own sake. It is that the cost of being wrong stops being recoverable.
Pick the one purchase you are actually weighing right now, whether it is a car, a piece of furniture, or something for the kids, and run it through the three questions above before you look at a single price. If it lands in the false-economy list, stop comparing prices altogether and shop new. If it does not, the used listing you already had your eye on is probably the smarter buy, and now you know why.