Did I read this correctly? You are going to go to ICN from SIN via SFO?
If this is on United you will be going to SFO from SIN via NRT. You would make two trips across the Pacific to get EQMs and save less than $200? I don't know if that qualifies you as crazy, but it points to an unhealthy obsession for accumulating miles. <g>
I doubt UA will let you use one SWU from SIN-SFO-ICN since they are two different tickets. Also, when I traveled from DEN-SIN in January I couldn't get an upgrade on the NRT-SIN or the SIN-NRT segments. Less business class seats since they switched to a 777 on that route.
Happy flying!