Let me offer a concurring opinion - Uber seems incredible expensive for two or three trips a week, from my experience. It works best when you're with a group of friends/family members and you are all drinking or don't feel like dealing with driving and parking. I would never consider it as an option like a normal cab for when I just need to do the week's grocery shopping or run out to get something at midnight, when the light rail might have shut down for the day. The only city where I ever used it was Denver, actually. Is this different from others' experiences?

As a side note - can't you drive two hours to a mountain from most East Coast cities? The Catskills are only 2.5 hours from NYC. I thought mountains were much more accessible in Denver than a two-hour car ride.