Note small engine, but supreme screw-up:
Had an nice '72 Corvette with a 4-speed. Ran fine, and I bought my first set of drive-up ramps so I could do my own oil changes. Bought a Haynes repair manual.
One day, was changing the oil and leafing through the manual looking for anything else I should be checking under the car. "Transmission gear oil Level" caught my eye. Okay, seems you just remove the inspection plug from the side of the transmission, and the gear oil should be right up at the same level as the hole. Easy enough.
I unscrewed the plug, and yikes! A BUNCH of oil drained out. "Golly!" sez I, "Wonder why this transmission has so much extra oil? It's only supposed to be filled up the the hole?" I let about a 1/2 to 3/4 of a quart drain out, replace the plug and was glad I checked!
Sure was smart of me! Got all that "extra" oil out of there.
Of course, I failed to realize you only check the level of oil when the CAR is on a flat LEVEL surface. With those front wheels ramped up a good foot in the air, all that precious gear oil just flowed right onto the garage floor.
It took about 2 weeks, but the transmission finally self-destructed from a lack of oil. It was a painful, $1,100 (1982 dollars) lesson.
P.S.:
Was changing the oil in the wife's Mazda. Pulled the filter off, but neglected to notice the o-ring on the filter decided to stay attached to the engine, not the filter. Put on the new filter, and got it hand-tight as normal. The double o-rings left a nice 1/4" gap all around the filter (!).
Added 5 new quarts of Castrol, sat in the driver's seat with the car still up on ramps, and started the engine. Heard an "unusual" gurgle, and my eyes got real wide when I looked down and saw a ever-expanding puddle of fresh oil being pumped out of the gap and onto the garage floor. Took about 2 seconds to empty it. What mess!