Your not looking at it correctly. If LAX-LIH has 4 seats avail in R that's what it shows (R4). If the connecting flight ORD-LAX only has 2 seats in R then it shows R2 for the whole routing. If there are no R seats for the first flight then the whole thing shows R0 This has NOTHING to do w the ability to upgrade the LAX-LIH segment. If it shows R4 then you can upgrade just that segment
They designed the computer to show you whats avail for your entire routing. I think it's a terrible "glitch" but it's not as bad as what you thought it was saying