Q1: To the extent that check-in time becomes the determinate variable and assuming you OLCI 24 hours before flight, will someone on a connecting flight (who can check in >24 hours than the gateway flight) always trump a passenger only traveling from the gateway (e.g., LAS-SFO-HKG passenger will always trump passenger of equal status flying SFO-HKG) where both check-in at 24 hours pre first flight?
Q1: Correct, but keep in mind fare class comes before time added to waitlist. So, assuming two people have the same status and same fare class, that is the ultimate factor.