Apart from dropping my Ethos 21mm (which fortunately only resulted in a minor scratch...phewww) I really haven't had major incidents with my "personal gear".
However, when I was working at Perth Observatory one night I was in the middle of an photometry observing run (on a comet) when I went to reposition the dome onto a standard star (to take a reading) the dome stopped rotating, so I moved it back a bit, as I thought it was stuck slightly, and then tried to move it forward again. It only moved a short distance and stopped again. Damn, I though, what is going on here, until I looked down and saw "hydraulic oil" running across the floor. The dome rotation was operated by hydraulic motors due to its mass and the tank was located in a side room in the dome. Anyway the hydraulic hose burst at the tank and whilst trying to move the dome, I stupidly pumped the tank nearly dry (about 50 litres of oil).
Now, I can't remember how many steps there were going up to the dome of the 24", but it was a lot. I had to find a bucket and carry sand up to the dome to contain the oil. After many trips up and down the stairs, I was totally knackered, and I mean totally. After getting my breath back I proceeded to clean the oil up and it took about six hours, as I then had to carry many bucket fulls of oil back down from the dome.
It was my worst night of observing ever, that wasn't related to cloud. In fact it was a crisp cold night with excellent transparency. Damn it. I had my "moon" boots and, and still have them, and they are well and truly well oiled now.
The observatory has some basic sleeping quarters at the base of the dome, so I just went to sleep there as I was totally exhausted.
I had other incidents at the observatory, related to equipment failure, but that was, by far, the worst. I will never forget that night!