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? 
otterbein
You can start off by buying used components. This allows you to affordably find what you like. Later you can buy new components or higher quality used components. Of course, Audiogon is a great place to do this. 
As a previous writer stated don't be afraid to ask on this and other forums for in home auditions, we all enjoy meeting new people and sharing knowledge and our systems. You can also try Audiocircle , audioasylum and Usaudiomart. Good luck enjoy the listening.
Be not afraid of buying used (but not abused) equipment....

Everything I own, with the exception of 3 pieces of 'pro audio' is used.

Starting 'small' is nothing to be embarrassed about.....but being 'picky' about What and within budget basically (imho) resides in your choice of speakers.

Like us, they have distinctive 'voices', and traits within that....That will take the bulk of your time to find what you like....

The majority of 'upstream' equipment has decent and acceptable specs and response.  It's only when one has developed personal preferences as to how it responds to the music you like that the more minutia become relevant and important to your enjoyment.

Buy the best you can rationalize for what you've in mind for your ears.

Pay attention to the space that will reside in.
'Bright' speakers in a 'live' room can be a bit much, as will the inverse of that....  One way to consider it is to approach the endeavor as a balancing act.

Don't be afraid to invoke the SAF option (if available *G*); they do tend to have an edge of sorts, and they generally have to live with the system as well.

The KISS factor is important.  She may want to use it as well.  It shouldn't require a Phd to play a CD or even an LP....

My SigOther learned how to use a destat gun, a fibre brush, and a cuing lever.  It's not rocket science, just good technique....;)

Go forth and enjoy the journey. *S*

Regards, J
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.