Spotted a great tool in the Superior booth, designed to drain the oil from a horizontal oil filter. Just clamp it on, attach a hose to the nipple, and screw in the tee handle, which neatly punches a small hole in the filter case.
Leave it and do something else for a while, then return to an empty filter, which unscrews without a mess. The tool is called an "Easy Drain", and it's made by Tempest. See your favorite dealer.