After serious thinking Scott wrote :
Would there be an argument for putting both leads into the same side,
so each terminal has two wires going into it, then the wires are in
physical contact and the space is better filled?

Always aim to as near as possible fill the space in a connector, to
minimise resistance. Sometimes you can put two wires in from opposite
ends and long enough to be caught by both screws. Sometimes you can
feed both in from one end. The idea is to minimise the current flowing
through the connectors metalwork, by having the copper side by side.
Fold them over too, if you possibly can.

In the days when we used to solder cable lugs on large cables, if the
lug's socket was a little large, we would be taught to build the copper
up with a layer of copper wire wound around it, rather than rely on the
lead solder.