Not having your tire inflated to get full tread contact will cause either the inside treads or outside treads to wear faster.
This "test" only works when the tires are newish, once you wear them down they will be worn flat at the pressure you were running. The problem with that is if you started with the tire overinflated only the middle tread is worn down until the rest contacts. When you drop the tire pressure after that happens the middle pulls up which is what he meant by cupping I think. In "correct" tire terms cupping is wear on the blocks of tread, usually caused by misalignment or suspension issues. Basically chunks of the tread are missing, aka "cupped" treads.
To check for full tread contact you're supposed to take some chalk etc and run a line across the tread from one side of the tire to the other. Then drive down the street and back. If all of the line has worn off evenly you're good. If you only wore off the middle you have too much air, and just the outside means they are underinflated and the middle is "cupping" upward.
That test isn't going to work out very well due to the snow and all. What I did (cause I got sick of driving around the block and jumping in and out of my jeep) is parked in the garage (nice flat smooth surface) and slid a piece of thin cardboard under my tire. If I could slide it under no problem I knew there was too much pressure and the tire was sitting on the middle of the tread. Once I started getting some resistance I knew I was close.