Headphones

Nope, not worth it.

Trained ears might be able to hear small difference since they know what kind of flaw they are looking for.
For normal people most likely wont notice a difference.

I personally listen to my i4 in bluetooth almost all the time.
The thing I'm looking for in a song is usually certain moment when the beat slaps and I just match my walking pace to the song.

Not something like mmm, the cymbal sound lacking that micro hiss sound.

The only thing that triggers me usually when the song itself is a bit too low in quality.
Which is usually the problem with youtube music, since they sometimes just put user uploaded video that have 96kbps audio or something.

You can always try though, always do it with doubt in mind. Otherwise placeboost will magically increase your hearing skill.

But in the end even you can notice the difference, what you get is not enjoyment. But annoyance when you notice certain part of the song is not lossless enough.