Do you listen to equipment or music.

My testing playlist is my general favorites. To me, the fact i know my favorites inside out upside down is the best reason to use them.When I get a surprise.. something I really never heard or noticed before THAT gets my attention when auditioning some new equipment.

In my case I buy equipment that I think will inprove the sound of the music in my system When that upgrade happens I listen to the music the upgrade produces not the equipment itself. 

It’s been 9 months and 7 days

Josh, give it another week and you'll be considered late term. : )

Again..tenured music lover.  As a hobby, it's natural to want to move on and "get closer" over time.  For me, the home run is the music, and no nostalgia to what gets me there.  I don't marry the gear.  I'm fully awakened when a tweak or gear improvement "freshens" your entire collection, yet again!  Nor am I saddened when things seem to get a little tired and boring.  It simply means it's time to get more creative somewhere in your system.  There is ALWAYS something one can do, even if it simply means turning your electrical panel mains and circuits on-off a couple times every 6 months.  Loudspeaker placement and DSP adjustments also can freshen everything without cost...sometimes I prefer more center-fill, sometime more depth of field or stage-width.  It's all an amazing illusion, after all, play with it!  More peace, Pin.

Ok, this may be a little off point, but you'll see - it ties in.

I have a sister that is clinically OCD. She will sometimes clean and re- arrange her house until she literally drops from exhaustion. She got this thing, awhile back, about collecting rocks to line her driveway. After collecting a good number of various sized and shaped rocks (on every walk she took, on every ride she took, from neighbors wanting to get rid of their rocks, etc. etc.) ranging from 20 - 40 lbs. she got enough to nicely line her driveway. Her OCD would not let her stop at that, now she has a one acre sized yard covered with pile after pile of rocks. I jokingly told her that she should contact Mr. T. and offer to build his wall and could even bring her own rocks - don't think she appreciated the humor.
My point is that, we as audiophiles, may get a little OCD and let a continual need for upgrades, tweaks and changes, take the place of periodically just sitting back, for a bit, to enjoy the music.......Jim