The next question is: Is it worth not upgrading on a flight and hoping that fare/status secures a op upgrade?

IMHO, upgrades on domestic flights less than 3 hours are really not worth upgrade. The meals served today are certainly not worth the upgrade. However, FLF (Full Load Fridays) are worth the upgrade using certs. I have no clue regarding international flights with exception of MEX, where I certainly would upgrade. MEX-ORD/SFO/LAX is basically a transcon anyway but I would still upgrade.