Inclined plane and pendulum problem using Newton's Second Law factoring in resistance?

A friend asked me to help him with his physics. It's been a long time since I've taken physics, so I don't want to give him the wrong answers. He has two questions: If two objects of different m are dropped and land at the top of an inclined plane at approximately the same time, will they roll down together? Also, if two objects of different m are swung from the same length pendulum and through the same angle, will they swing together? I'm inclined to answer no to both questions; for the pendulum question, because the heavier object has more inertia and so the air resistance does not affect it as much, and for the inclined plane question, because of friction. For some reason, though, I remember that the lighter object will roll down first although that makes no sense in my head. Also, how would I further explain this to him using Newton's laws?