I don't know why you're making such a big deal out of this - is it about just "scoring points" - I'm getting a bit sick of it to be honest. But lets play the game.
I am not confused. You don't know me, nor the extent of my knowledge. Note that I haven't labeled you - so please have the courtesy to avoid doing so to me. Thanks. I also didn't say it was better or worse - I simply said it was not required (in the instance the OP described) to set the bit depth to the highest possible setting.
Now lets go through your bullet points:
Here are a few situations where setting it to 16 bit is strictly worse than 24 bit.
Playing anything that is not encoded in a lossless PCM format.
Why would it be worse - which is what you stated? Its a lossy file - so 99% of the time it'll be 16 bit depth at 44.1. What possible
audible gain are you going to get by setting it higher? Answer - there is none.
Here are a few situations where setting it to 16 bit is strictly worse than 24 bit.
Playing anything encoded in a lossless PCM format at higher than 16 bits.
Well unless he specifically wants to run in bit perfect (WASAPI/ASIO), again how can it be worse when there is enough dynamic range in 16bit that any difference is going to be inaudible.
Here are a few situations where setting it to 16 bit is strictly worse than 24 bit.
Playing 16 bit lossless PCM audio at anything other than 100% volume.
Again - go and do some real world tests and see if you can hear quantization noise - for normal playback you won't.
Here are a few situations where setting it to 16 bit is strictly worse than 24 bit.
Playing anything that does not match the chosen sample rate
Who's getting confused - pretty sure we were discussing bit depth.
Here are a few situations where setting it to 16 bit is strictly worse than 24 bit.
Using any DSP or EQ.
Mixing multiple audio sources.
I'm quoting these two together. The OP mentioned listening - nothing about recording or mixing samples. Even with EQ or DSP (and if he's asking the sorts of general questions he is, any EQ would be relatively simple don't you think), as long as he's not applying cumulative EQ and mixing multi-layered tracks, he's not going to need 144 dB of dynamic range. I agree the higher bit depth if he's mixing and recording, and there it is definitely worth going to 24 bit - but you're using a specific case which the OP didn't mention.
Now - can I make a suggestion - none of this is helping the OP at all. I stand by my initial statement that there is no need to set the bit depth for a listening environment to above 16 bits (I will add here "unless specifically required for recording / complex processing). For the majority of his use, 16 bit will fully capture the dynamic range for everyday playback, and any difference is going to be inaudible. If you wish to carry on this debate, I suggest we take it to Sound Science, because all its doing is creating a point scoring debate here.