I don't think our hills are very steep. It's rolling glacial formed hills, not mountains. I also wondered about what's better-new un-walked on snow, or someone's previously walked trail. I think we started out aggressively without working up to a goal, but like I said, we don't always get the right kind of snow. We're going to REI, and I think maybe he could try a waterproof trail running type shoe with gaiters. He never buys anything for himself, so I'm not sure if I can talk him into a new pair of snowshoes or not.