That's obviously unworkable if you consider that even the Supreme Court's interpretation of fundamental rights can change over time. If a future Supreme Court overturns a prior Supreme Court decision in a way that expands a particular right, do we punish all the judges who followed the previous precedent? If we do, then we have a judicial system that encourages individual judges to ignore the Supreme Court, which doesn't seem like a good setup.

But more fundamentally, the system you're proposing doesn't just incentivize judges to err on the side of caution, it incentivizes them to never rule in favor of the government and just punt the decision to the next level. If the cost of ever being overturned on appeal in favor of an individual's rights is losing their job, while there is no corresponding downside of ruling the other way, there's basically no reason to ever risk granting a warrant, for example.