Jackson Hole is one of the few resorts where the mythology still feels connected to the mountain. The tram, the steeps, the Tetons, and the town all create a big, serious ski trip. But Jackson should be recommended honestly, because its best qualities are exactly what can make it wrong for cautious skiers.
For strong skiers, the draw is obvious. Jackson has terrain that feels consequential, a western setting that doesn't need embellishment, and enough challenge to make a trip feel earned. It isn't just a famous name on a map.
For mixed groups, the story is more complicated. There's intermediate skiing, but the mountain's identity leans advanced, and the cost of the trip raises the stakes. You don't want to discover on day one that half the group is intimidated.