I live an hour and a half from the nearest decent hill. It is definitely nice to drive with someone, especially coming back because I'm tired from a full day of skiing, it's dark out, and I drive through a park so there's tons of deer and other animals.
Other than that, I find that I progress more in a group, as I see what they do, and I want to match it or do better. I find I'm less confident by myself, but that's just my own preference.
In my own experience, I find it is easier to find someone to ride with before you go to the resort. At least where I live, a lot of the boarders/skiers already have their groups and aren't usually looking for extras.