There just isn’t a one-size-fits-all answer as to whether it is cheaper and/or more time efficient to drive or fly. In general, short distances, small town destination, and many travelers favor driving while long distances, large cities, and fewer travelers tip the balance towards flying. You’ll simply have to work out the details based on your own trip, your own budget, and your own preferences. Personally, I would drive for either of your proposed itineraries.
You can almost guarantee that you will see snow at some time during those drives, but as I pointed out before, and as your own experience suggests, if you can afford to sit out the storm and let the road crews do their work, the highways will be open and eminently drivable in short order.
AZBuck