I'm not sure if what you're doing counts as fun or sad. It's always hard, at least for me, to see what becomes of people and their stuff as they get older and their health fails. On the other hand Fred is letting you do at least some of what needs to be done to preserve what's left. Far better that someone who cares about the machines gets in there than a scrapper.
Grab every bobbin he's willing to let leave. The new ones don't fit old machines as well as the vintage ones do. I know for a fact the width at the outer rim on new class 66 bobbins is smaller than on the vintage ones. You're lucky if they will fit vintage bobbin winders correctly.
Rodney