I have had some crackers as i went through a stage in the 80's where i would never pay more than £100 for a car.
A 1969 Hillman imp was the worst, it used to break the accelerator cable once a month until i fitted a rally!!!! version, gear stick broke off in my hand when changing into second gear joining the motorway had to drive it for 20 miles in second, took me 7hrs to change the clutch as the bolts that held the rear panel on where seized and rounded off, in the end it blew the head gasket.
Austin Ambassador front wheel fell off on roundabout, hydrolastic suspension collapsed, took it into garage and they fixed the wrong side, as they could not tell which side was Broken it was that bad, also had to wedge three of the windows closed with wooden blocks.
Volvo 144, i bought this after it had been standing in a field for 4 months, steering wandered all over the place and you needed to be Popeye to turn the wheel, I left the grass growing out of the vinyl roof, took it for mot and the body had detached itself from the chassis, but what do you want for £25 and it was taxed.
Mini 850 van with windows in it and a homemade back seat, took me 11 hours from London to Manchester as I had to leave the M1 at Watford and use the A roads as it would not go faster that 50mph which meant I was stuck with the trucks and in torrential rain it misted up, the windscreen leaked and the wipers could not clear the rain away, I broke down on this journey but luckily it was only a wire that had come off the coil.
Another Mini (1964 version) in Australia, this was so good that I left it in the short term car park when I flew home, the most useful thing about it was the door pockets would hold ice and a six pack off beer, I also set the rear seat on fire with a discarded cigarette, but that was not the cars fault.
Happy days.