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
“how does one gain listening experience without blindly buying and trying”

@otterbein,

I would suggest join a local audiophile club or attend audio shows. The two biggest audio shows in NA (assuming you’re in America) are AXPONA and RMAF.

Not sure if there are any audio shops around you...look them up and see if anything interests you as most of the high end dealers are now operate by appointment only.
millercarbon gives some good advice in terms of using good recordings to work with a system. Growth and appreciation of musical genres and quality recordings is a most gratifying aspect of the hobby. Good advice. However, this is but one aspect of the hobby, and it is not necessary to spend inordinate time on it in order to build superior audio systems. i.e. knowing the background of the recording does nothing to help calibrate a superior system; use of such a recording is all that is necessary. Actually, it's not even absolutely necessary to use such recordings to advance an audio system, but imo they certainly do aid in advancement of a system more than poor recordings. I encourage use of a very wide range of recordings, including poor ones, to assess how a rig is developed. But, involvement with the recording process is a tried and true vector of satisfaction in the hobby. Just watch out that it doesn't turn you into a Mediaphile, i.e. buying multiple copies of the same recording and impoverishing your chance to elevate the rig! You can DESTROY your entire audiophile future by making such a mistake!  ;) 

I must admit that my tastes have been expanded positively through the years by growing appreciation of great recordings. I have a friend who is fantastic at procurement of such recordings, and his guidance has been great! 

If you would like to educate yourself on the topics of burn in and warm up, I encourage you to read my comparisons I wrote about in an article that appears at Dagogo.com under the title;  Audiophile Law: Thou Shalt Not Overemphasize Burn In

I was a budget audiophile for many years. I wish to discuss your characterization of this being a "rich man's hobby". I worked for the better part of 30 years consistently putting some money into the hobby nearly every year to accomplish my goals. I do not consider myself rich in the monetary sense, but disciplined. You also can accomplish amazing goals in this, or any other hobby, if you work hard enough to accomplish them, and I encourage you to do so. It IS a rich man's hobby if your goal is to attain sound in the range of SOTA (state-of-the-art), and get there fast.  :) 

I way I read the OP, he was talking about the *range* of various and different components that some people have clapped ears on.

No short answer, and none ideal: audio shows, audio societies, audiophile friend, big cities with multiple dealers.  Otherwise, yes, significant funds and a strong back to swop in and out components.