Up is very much not free. It costs a lot of energy to keep something suspended in mid-air. Airplanes that move hundreds of people are already under scrutiny for how much energy they use, there's absolutely no way we'd accept personal flying machines. Personal automobiles that can rest firmly on the ground are already criticized for their consumption even without having to lift off the earth.

Down is much cheaper.

You presume boring will always be prohibitively expensive.