As much as I try, I just don't get it........

Listening thru headphones is a better experience.

But I would consider the source; who is producing the video. Is it an amateur or a professional? Try listening to the Deja Vu Audio videos. They sell high-end components and also do custom builds. I really get a sense of the SQ of their audio setups.

And I agree with MC; use all the experience you have learned in listening to music. There are tonal qualities, dynamics, nuances in reproducing music. I know you have what it takes to be a good listener based upon your postings.

This is crazy broad strokes, but there's a progression audiophiles tend to go through en route to becoming a good listener/evaluator. 

We start off being able to notice tone, frequency, and volume. When you hear people talk about cables being tone controls, this is where its coming from. You can tell the level of the audiophile by the language used. 

Next they start to notice things like dynamics, and that there's a sound stage. Dynamics is harder to differentiate than you might think, because there's things like bass extension and hyped treble can trick you into thinking its more dynamic. Also there's the obvious body slam impact aspect of dynamics, and then there's micro-dynamics, the subtle quiver or tremolo of a voice or string or whatever that triggers that hair on the back of the neck "this is real" kind of feeling. 

Usually most audiophiles up to this point are pretty well convinced of the need to have certain "reference tracks" they play at "reference volume" on something called a "reference system." They need to keep it simple because they haven't yet learned to differentiate, let alone mentally correct for, the effects of these things. 

For sure this is triggering some "aha" moments and recognition of a lot of what goes on around here. 

This is about where most stop, and its understandable, because its tough. The scope of what we're hearing expands into hard to describe things like timbre, attack and decay, air (most everyone blows this one), and the list goes on and on.  

Practice makes perfect. Here's another one https://www.youtube.com/watch?v=AWp48WzlkMoThere's a whole bunch of them on this channel. They're great because even though the records change there's a bunch with the same table, cart and phono stage, and even DAC, and when these things change he lets you know.  

Keep in mind at this stage of the game you're simply trying to notice the similarities. You're not trying to figure out what these things sound like in any kind of absolute sense. What they would sound like in your system. Forget that. Just listen and try and get a handle on what's the same. Patience helps. I probably listened to that Christopher Cross a dozen times now. 

Mr Decibel, you are absolutely correct. Listening to these videos or files is a complete waste of time. It is a blatantly unsatisfactory way to make any determination about anything. 

I wish some of these posters would practice what they preach!
As for using YT for evaluating an audio component (listening), what a joke. You really can't go to a dealer and listen to a set of speakers and think they will sound like that in your home, in your room, with your components. Same goes for an amp/dac/preamp, you need to evaluate these components using your system to see how the synergy is between the components.
This is like test driving a car from a YT video. Impossible!
YT as well as on the web, you can read reviews and check out how people are using the product you are evaluating/looking at, but even then, you don't know how smart the guy is that is presenting.

I'm not listening to these YouTube videos to audition equipment. I'm checking out somebody's system. There are so many with terrible sound. And it's not representative of listening at home.

Sometimes I trade audio files with a friend thru email. He knows my system and I know his.