Challenge: Travel- On Foot.
I have never envied hobbit feet. They seem to me too similar to my own feet to be well suited to walking in the winter snow or slush.
I wonder at the depth of callus that is required to make walking on scrubland pain free, when one might easily encounter thorns and pieces of sharp flint. And whilst there is hair it does not seem adequate, to me, to keep feet warm when ice covers ponds and rivers.
No, even when the soles of my boots wear thin and my woolen socks need darning, I do not envy hobbit feet.