I am torn.
I could cite the $3500 I spent in 3rd year university for my initial "real" audio system - Totem speakers, Sugden amp, Atlantis stands, a Sony changer, and a bunch of music - it lead me to the path of music lover, via a good system.
I could cite the $1000 or so I have in my Bolder SB3 - completely revolutionized the way I use my system, and the way I use music.
In the end, I think it is money I did not spend that was best invested. My parents spend $1000's on music lessons for me over the 10 years I played violin (achieved the 9th conservatory level), and this honed my musical ear, and put me in touch with how music can make me feel - self generated, live, or reproduced.
Have I ever spend bad money on audio? Another thread perhaps!