The worst single incident was when I accidentally swapped rod caps on two adjoining rods - ended up spinning a bearing about 200 miles from home. Limped it back and had to replace the crank and those two rods.
I guess the second one would have been when I had a fram oil filter blow off my bike at 13K RPM in top gear. Luckily, the safety wire kept the filter inside the fairing, which also gave me the opportunity to see that it was not due to an error on my part - it wasn't a DIY failure, but if I had a shop to it, they would have used an OEM filter and I wouldn't have lost an engine to the Fram gods.
The other things that happened were anything I touched on the (at the time) 3 year old, 40K mile Audi would break off. Check the oil, dipstick broke - try to fish it out, tube broke. Change multiple PCV check and jet valves (turbo) , plastic elbows break, oil-soaked hoses disintegrate. Try to open the hood to replace the alternator due to a bad clutch, the hood latch broke. Replace fan belt, shortly afterwards, an idler pulley broke sending the belt into the radiator. Change the timing belt ahead of schedule because one of the bad check valves allowed the crankcase to pressurize and push out the cam seals as well as many other rubber gaskets, and frequently the dip-stick. While doing that (now at about 50K) see that the rear timing chain tensioner was broken (it had a belt in the front and chain in the back) and one cam was flapping around - not noticed because I thought it was the alternator clutch making noise (which it was, just not that particular noise)
Essentially, every single thing I touched on that car disintegrated. It's the first car I ever remember selling before 65K miles, and we were the first owner. I don't count the new transmission and drive shafts and other things that were covered under warranty because they weren't DIY. The car drove very nicely though.