does moving an object a greater amount of distance always require a greater amount of work? Why or why not?

Yes, moving an object a greater amount of distance always requires a greater amount of work.

Explanation:

Take a look at the formula written below,

W = F x D,

Where W = work, F = Force, D = Distance

You can see the Force and Distance have a multiplication sign between them, indicating that Work is directly proportional to both Force and Distance, or in other words -

Work α Distance

If that is so, an increase in distance should always mean an increase in work, ( vice versa ) and a decrease in distance should always mean a decrease in work ( vice versa ).