Earlier quoted context omitted.
> are there any cases where it would it be impossible to empirically demonstrate that at least the proponent of the lower figure was wrong? Isn't it more interesting to examine a situation where it would be possible to empirically demonstrate that the proponent of the lower figure was wrong?
In that case we could objectively say that one value of S does not yield F for that system (given that F is defined as a maximum), but this would not resolve the general question of subjectivity.
I have a partitioned box full of air at room temperature and pressure in both partitions. There's a frictionless door that can be open and closed by an ultrafast servomechanism. The servo is connected to a computer which will read a very long bitstring from a magnetic hard-drive platter at a high frequency and open the door when the bit is '1' and close it when the bit is '0'.
Admittedly, this mechanism would be hard to construct in practice, but I hope it's clear enough as a thought experiment.
Now if you're familiar with Maxwell's demon, you'll agree that there are particular, albeit rare, joint configurations of gas microstate and hard drive bitstring, such that after the servo has finished its last motion, the gas will have been separated into hot and cold on either side of the partition. This temperature difference can be used to extract work.
For each possible bitstring on the drive, there are certain corresponding microstates of gas that will maximize the free energy extracted by this process.
And for each possible microstate of the gas, there are certain corresponding bitstrings that will maximize the free energy extracted by this process.
(For the vast majority of other combinations of hard drive bitstring and gas microstate, the operation will have no effect).
The claim "entropy is subjective" is basically just an acknowledgement that the energy extractable from the gas is dependent on both the state of the gas itself and also the data written to the hard drive. It means that two experimenters, tasked with writing the initial data on the hard drive to extract as much work as possible from the gas, will have different levels of success depending on whether they know the particular microstate of the gas (and can thus select the corresponding optimal bitstring) or if they don't know the microstate of the gas beyond "a box at room temperature and pressure", and have to guess a bitstring based on only that. And when the operation is successful, we can describe the data on the hard drive as "information about the gas microstate that was used to extract work".
This experiment, of course, is so impractical that it sounds ridiculous. But we can make a more controlled version of it on the small scale, with excited trapped atoms, and actually make it work.