What has been your costliest mistake in this hobby?

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.

Mcintosh  MVP 891, thinking it would be good($5000)

     Shorted out all of my Audire electronics!     Two amps and two preamps (used to keep subs in phase while being able to separately control bass), and my CD player were fried.  The battery powered head amp had been my mainstay. 
     When an old college roommate reversed the batteries in this POCO, it killed it, just as it had in college when the same idiot did this. I was without, so I traded it and one of my Diffet 3's for a Diffet 2 with the POCO built in. 
     About a year later, the Diffet 2 started taking longer and longer to come on.  I posted a photo of its innards, and a nice person on the internet pointed out two little caps that powered up a pair of reed switches. If I had left it on, there would have been no issues, at least for a while 
     I ordered the caps and arranged to get them soldered in, but first, I had to get involved and decided to test the transformer.  Putting the test leads on the terminals, to check output power, I shorted a lead against the silver wire that provided power to a row of 120 volt outlets, thereby sending 120 volts through the entire system output interconnects, and apparently through the CD inputs, somehow missing the KT-917 tuner and XM radio, which must have been switched out. 
     I was at least grateful the tuner was not damaged.

I've been pretty lucky with my purchases, even luckier connecting with people who gave me great advice, which guided me to "listen for myself".