Go and try either way- what you will find is that the file feels
smoother and chatters less when you are filing with the set. The
difference is enough to notice right away with no confusion. If you
are just starting out take and ink the teeth up with a marking pen as
it will give you a nice visual proof of how the file is engaging the
tooth.
Trying to visualize the saw in my head just makes it too complicated.
If you are dropping the file handle that is to produce a type of
sloping gullet which the geezers claim is better in softwoods.