I don't see that this some sign of systemic dysfunction. Given the significant amount of time and effort that is expended before a legal dispute is considered

I don't see that this some sign of systemic dysfunction. Given the significant amount of time and effort that is expended before a legal dispute is considered by SCOTUS, it stands to reason that the arguments would be sufficiently nuanced at that stage. If the highest court of the land doesn't sweat the details, why would lower courts or any other aspect of our legal system be reasonably expected to do so? In any reasonably complex system (legal or otherwise), it should make sense that the technicalities do matter, and that the supreme decision making body in that system should consider those carefully due to the outsized influence it holds.