Wasn’t me, but my uncle:
He bought a used cabin cruiser boat, maybe 25-30 feet long. It was well used, and all of the upholstery, wood trim, etc. had to be replaced, the metal bits de-rusted, and paint applied all over. He spent a few months working on this when he had free time.
Eventually he was finished, and the boat was looking good!
For some reason, (and don’t ask me why 'cause I don’t know!) he decided to see how the boat floated… so he hooked the boat trailer to the back of his pickup truck and hauled it around behind his house where he had a small pond; perhaps twice the size of the boat in diameter.
He began backing the boat and trailer into the water.
As he slowly backed into the pond, he realized that the boat wasn’t floating quite the way it should have been, and he stopped, applied the parking brake, and jumped out to investigate.
It turned out that he had neglected to put the plug into the drain hole in the back of the boat, and his boat was slowly filling with water and settling back onto the trailer he had been trying to float it off!
He jumped back into the truck to pull the boat and trailer out, but by then enough water had entered the boat that he merely succeeded in burying his 2 rear tires in mud. No problem, he popped it into 4 wheel drive. And shortly all 4 wheels were entrenched and the truck axles were at ground level.
As he was the only person at home at the time, and there were no other vehicles, he walked about 2 miles up the road to a neighboring farm to borrow their tractor.
Which he got stuck in the mud in front of the truck a short while later.
A longer walk up the road to another farm resulted, an hour or so later, in yet a second tractor stuck in the mud in front of the first tractor, the truck, and the now almost completely submerged boat and trailer.
A backhoe was eventually required to un-stick everything, and my uncle started over on the remodel of the boat…
(true story! AND, several months later he, my aunt and several cousins were on Lake Eerie in the boat, hit a partially submerged log, sunk the boat for good, and had to all swim a mile or so to shore…)