The last thing I do before I put my car away for the Winter is to give her a half-a$$
oil change via a vacuum pump attached to a big glass wine bottle -- I don't even bother giving her a real
oil & filter drain until Spring. If you are compulsive enough to want to get every drop out of your
oil cooler then catheterizing her with this would probably be the easiest way. Just unbolt one of the oil cooler lines and then snake the plastic vacuum hose in to the bowels of the cooler and suck it dry. Or, you could do like me and just not bother at all.
Here's a shot though of my half-a$$ oil changing gizmo:
