I have to gigle + giggle. There are so many. My biggest off the top of my head was my first car. It wasn't really expensive and I afforded it easily. A '53 Ford Victoria two door with a 341 stuffed into it. I bought it from a high school friend's dad after graduating. It was to be my first hot rod.
Well it drove home okay. The next morning I went to work at the gas station I worked at. I got through town and the brakes felt weird. I turned into the back parking lot, put on the brakes, oopps! the brake pedal went to the floor. I had a choice hit the dumpster in front a a 2ft ditch or go in the ditch. I choose the dumpster and knocked it into the ditch. LOL
Anyway, I had it towed back to that friend's dad and he refunded my money - $150 in '72. Today a clean version is worth over $16,000. Hot rod versions done well over $20,000. Besides, they are cool cars :)