What has been your costliest mistake in this hobby?

I purchased a pair of Von Schweikert VR33 speakers used for the retail price of new because there was a 6-9 month build time and I had to have them. After I received them I realized they sounded terrible in my room. I tried all the usual fixes like moving them, putting pillows in spots where I thought things sounded better, etc.

A year + later, my wife mentioned I hadn’t listened to the stereo in many months and only a few times since I got the VS speakers.  I Vacillated another 6 months before I admitted to myself that I hated the speakers. I then bought into the Golden Ear line and I am extremely happy. To finish my story, I sold the Von Schweikert speakers for 66% less than what I paid for them, and also lost my shirt on shipping.

My most costly mistake...like most, is knowing this hobby we all love so much will never end it's cost....sad but true...

Bought a pair of Higher Fidelity 138 monoblocks for a sweet deal. Very very powerful. But needed some love. Postponed that. Bought my first biamp cable, a vd hul Revelation. It had the most thick spades ever made. The cables were also very heavy so it tugged on the speaker terminal, and there wasn't any good connection with it too begin with due to thick spade

 1 day before Christmas 2018 I was blasting music, cables came loose and a ball of smoke erupted from my amps.  I really loved those van de Hull wires so kept them, happened again to the other monoblock 😭

Maybe 8 months later both amps worked better then ever: rebiased, new lv matched transistors. Didn't like the highs coming out the speakers sold them. But in hindsight it was a system mismatch

The guy who bought them couldn't believe his luck. 

Repairs: €760 down the drain 

I was lucky and bought a Theta gen VIII series 3

I was adament to play it in 220v. I had it modified to 220v (was original 120v) cost €550, -
Totall unnecessary... 

I quickly sold the unit because I didn't like the sound compared to the old Gen V-a I had.

But the ease the unit worked
Best volume control ever!!! No big jumps when pushing a button. When you want to hear music in the background you can still up it at least 5 steps volume wise. So you can hear everything, plus a little bass. Best audiophile background preamp ever
Dead quiet
Jitterjail 3 used on internerradio is a Revelation. What sounds crappy will sound stellar

Sold this gem for €550, - loss. But the loss is greater. My system is too complex, gf doesn't know how to use it. And spend thousands for better sound when I should have looked at function as well. 

Keep buying additional boxes

Falling for the early cd sales talk. It was many years and $ later the error of my ways was forgiven.