Re: #2 - Cups open side up or open side down:
The answer is both, but alternating. Stemmed wine glasses and most drinking glasses are wider at the top than they are at the base. If you alternate the glasses up/then down, you are not wasting space in the cupboard and a shelf that could hold 9 glasses with a 3 x 3 configuration could potentially hold 16 with a 4 x 4 configuration (depending on the dimensions of the glass of course).
That's a 78% increase in utilized capacity, and I didn't even need a stupid packaging engineering degree to figure it out.