Honestly, it depends a lot on your climate. If you live somewhere with freezing temperatures, winterizing is absolutely necessary. When water freezes in the pipes or pump, it can cause serious (and expensive) damage. Draining lines, lowering the water level, and adding antifreeze where needed protects your equipment and pool structure.
On the other hand, if you're in a milder climate where it rarely freezes, some people get away with just keeping the pool running at a low level all winter. But even then, leaving it uncovered can lead to a major cleanup in spring leaves, algae, stains, and more. The cost of chemicals and time to fix that mess might end up being more than what you’d spend to winterize properly.
So while your neighbor might be rolling the dice, winterizing is usually the safer long-term bet especially if you want to avoid surprises when spring rolls around.