Mine used to lose its brakes. Last time was down a really steep hill in Harrogate. Used handbrake and gears to screech to a halt about a foot from a junction. Foot to floor, nothing.
Managed to get it home (handbrake, gears) and the brake nipples had 'unscrewed themselves' as far as I could tell. Tighten up, fill up, bleed, all ok but after the horrors of the drum brakes then my disc upgrade not exactly being fantastic (and failing) I was finally glad to get shut of the thing and walked instead for a few months. As others mentioned, old mini was a great idea but only if you are handy with spanners and don't mind getting your hands mucky.
Worst shed I owned was a Citroen Bx. The pneumatic fluid ****ed out at every opportunity and I got quite proficient at driving about without a foot brake, power steering or suspension. When the clutch cable snapped as well, I became quite the expert at driving without steering, brakes, suspension or gears. And when the engine started clattering and cutting out every now and again (to mysteriously restart moments later) I only shrugged. Par for the course.
I think the final straw came when the door solenoid gave up and locked me in so I had to climb over the passenger side to get in and out. The car was trying to tell me something I think.
Can't see modern cars doing that, but I can see repair bills being higher as there's less for a diy mechanic to do with every new generation of car, hence £100+ an hour for labour...