Schwinn designed the Deluxe headset with a reversed top adjusting cone/cup on the top to carry increased bearing loads. The adjusting cone, is actually a "adjusting cup", and the stationary cone is press fit into the frame. It uses a #73 top bearing and a #2557 bottom bearing. It has not changed one bit in the last 70 years. The original poster's bearing is correctly positioned, the Schwinn Parts Catalog was incorrectly drawn in the 1960's. Your 2nd photo with the bearing installed is correct. If you are not sure just place the bearing into the "adjusting cup" (printed writing facing towards the ground) and put some downward pressure on the cup into the frame cone. Then reverse the bearing and try the test again, it will drag if placed like shown in your top installed photo.
I'm not making this stuff up.
John