Gaining listening experience without spending money

I am always blown away at how many folks on here have experience listening to so many different pieces of equipment. As an average dude loving this rich mans hobby, how does one gain listening experience without blindly buying and trying? 
Some of these suggestions might be useful for ordinary times, although perhaps not.  Depending where one lives and other circumstances, attending audio clubs and shows may not be an option.  And then they may not be the perfect place to demo gear, because ultimately the question is how will it sound in your system?
And now, with Covid 19, can you even meet as an Audio  Club?  And will crowded audio shows return, or be advisable to attend?
  I wish I had an easy question for the OP, but I don’t.  Ever since bricks and mortar stores have gone the way of the Dodo, comparison shopping in this hobby is difficult.  My preferred way is to have a component in my system for a few days.  Frequently this may involve paying a restocking fee of 15% if you don’t like it, plus shipping.  For something like a thousand dollar DAC (which the OP identified as something of interest in a different thread),that could potentially be a $200 dollar expense.  For something like floorstanding speakers in the $10K range, that’s 2 grand plus the sheer difficulty of moving them in and out of your dwelling, which is perhaps one reason that my speakers are going on 16 years of age.
Some good advice about but I am not sure if all this answers your questions. First see if there is a local audio club you can hear different systems and possibly borrow equipment so you get to hear other components in your system to see if you hear any differences and preferences.  Even if the club is not active right now, you may find some people willing to bring an amp or preamp over for you to her in your system.

Find a really good recording and get to know it very well. Backing vocals, separation of vocals and instruments, sound stage dimension, High frequencies, low frequencies, soft to loud and back dynamics/passages, cymbals, bongos (do they sound like someone is hitting a drum skin with a bong so you are hearing the wood of the bongo or like hitting a piece of cardboard - get to know the difference as many people really do hear this. etc. I change as I get bored with listening over and over to the same song but I prefer piano. IMO if the piano is correct, then the other things fall into place. Your should be able to hear the decay of the piano, what I call the box or wood of the piano so it doesn’t sound electronic or the notes fade to fast. Dean Peer is a bass guitar player and I use his recordings also especially the simple recordings of him and maybe a few other instruments.

Next read about different components and what attributes they offer. Start with tubes versus solid state, Class A, Digital components, etc. Learn what makes them sound the way they do by hearing them. Learn about AC filtering - this is what provides the separation and black background in a system.

For cabling - silver versus copper. Learn how they impact the sound.

So now that you know what you like, you can narrow down your choices. It is time consuming but now that you are educated you can sort through the crap and find what you prefer to hear.

To me dealers and shows are of no help. Most people go to a dealer or show and say hey that was a much higher cost then my stuff and it wasn’t better. That was the question I had many years ago. Why do my $2500 speakers sound as good as the $10,000 speakers everyone else says are much better.

How many times have you read well for $100K I was not impressed. There is a reason for that.

To many people chase the sound they are looking for instead of knowing what makes a system sound better. I was at a friends home recently. His friend and himself kept telling me that the system he had was just all of it. When I went to visit, he played me a song (not one that I was familiar with) but after the song knowing about his system, I pulled out one of his tweaks and the sound opened up and was more natural. I was also thinking to myself, how come these two guys could not hear what I was hearing? Everyone I know in this hobby always tells me, I have good ears. How did I know this, well I tried the same tweak in my system and heard how it impacted the sound. I also told him to do other things and recently he called me about swapping out his line conditioner for a $3000 one. I told him when I was there that his line conditioner was holding back the sound. I told him if he really wanted one to go with a different company’s that was much cheaper - better or not, I know what that one does. So again it comes down to listening and learning.

My system does not use any special cabling, tweaks, room treatments, AC filtering, etc. I hear what they do and so far it is not that as important to me overall. The reason is because I can change the sound with greater sonic impact by changing parts like capacitors, resistors, design changes, etc. I recently changed the resistors in a DeHavilland preamp. Just two good resistors changed that preamp to be more open, faster and dynamic - $20 in parts. Most products that are manufactured do not have any of these parts in them. What to know why? They are expensive! Why would a $20K amp have basic power supply capacitors in them, not high grade resistors (think Audio Note non-magnetic silver resistors), not even HexFred diodes. I only know a few manufacturers whose products are point-to-point wired product.

So begin by hearing different components and not focusing on the sound but what the differences are tube versus solid state, belt drive versus direct drive, copper versus silver, paper cones versus aluminum. What do you hear that is different? What do you hear that you think is better? IMO then you can understand what you like and how to build your system.

You do not have to spend a lot of money in this hobby to have a system that you like to listen to every day. It is that easy. Learning how to make your system sound better is the hard part.

Thanks for reading my dumb crap.

Happy Listening.

I'd put my $12,000 vinyl system up against many more expensive rigs. The trick is knowing about gear and taking your time. Understanding what makes things tick. Recognizing well-engineered classics. A poor choice in support platform and cheap tubes can compromise sound quality beyong belief. So many things can influence the end result. I've heard the good and the bad. Oftentimes, the bad had cost a lot more than the less-expensive good. Last note, imagine what you could buy if you weren't paying a $700+ car payment?
"You’re wrong because you don’t need any money at all. Because you don’t need to buy anything to be able to say why you like one amp over another. Because all you need is to be able to first hear, and then describe, the differences"
Says the man with a six-figure system...