I didn’t bother with a pool pillow the first year I closed my pool. Everyone online seemed split on it, and I figured since I had a decent winter cover, I’d be fine. That winter ended up being colder than usual, and we had a bunch of snow and freezing rain. When I opened the pool in the spring, the liner near one end looked stretched, and one of the rails had shifted slightly. Nothing major, but enough to make me regret skipping it.
The next season, I used a pillow, and while yeah, it deflated a little by the end of winter, I could see how it helped. The ice wasn’t pushing outward as much, and the weight seemed more evenly distributed under the cover. I also noticed way less water pooling on top. Since then, I’ve made it part of my regular winter prep, and it’s cheap, takes five minutes to set up, and gives me peace of mind.
So no, it’s probably not required, especially in milder climates, but if you get hard freezes or heavy snow where you are, I’d say it’s a smart extra step. For me, the small effort upfront has saved me more trouble later.