Your first step down the "audiophile" path? And sharing mine.

To share,.. my audio/hi-fi journey began with early Dynaco, 18 gauge zip cord, and BSR turntable.  But that was youthful music to my young ears.  The first step down the music/audio gear addiction was the following:

Yamaha CA-1000 amplifier
Yamaha CT-800 tuner
Yamaha YP-800 table with early ADC XLM
very early Monster wires/interconnects (which replaced 18g zip cord)
Advent cassette deck
Stacked Large Walnut Advents (top pair upside down)

And to feed my addiction I was getting British pressings from a store in well as the earliest MoFi when they came out (and there were 
a few other "special pressings" companies)

My path since has included many of the high-end companies you 
could name, but that early system is very much deep into my memories. 

With a large outdoor FM antenna with rotor, I could pick up late night 
FM stations that would compete with needed sleep time.  Ah, the joy 
of youth. 

I noticed I could play a CD on my system, play it on a friends system and it sounded different, play it in my car and hear yet another version, play it in a friends car and still another variation. I thought it was all related to speakers so in '97 I went into my first high end audio store and after listening to a different types, picked up my first pair of PSBs.