on paper, the worst car I've ever had is also one i wish i still had... It was my grandpa's 1987 Olds 98 Regency Brougham.
I inherited it after he passed, He had bought it used (w/ about 60k mi) in '90.
(replaced a 77 Olds 98 with the 400, and well over 200k mi, that had a severe case of bubble cancer all over. )
any how, in the time i had the car...(oct.98-aug.2001)
1)it ALWAYS had a leak (fairly significant) along the top of the windshield that i could never fully silicone closed.(went to work/school on more than a few days w/ wet pants)
2)window motors were ...geriatric... if you tried to use more than 1 @ a time, one of them would crawl to a stop while the other went up.
3)Tapes got stuck in the deck, so i got an aftermarket stereo w/ a cd player, which lead to....
4) car was stolen from me while i was @ a movie theater 100mi from home. only had liability (poor college kid, 12yr old car, w/115k mi...)so after it was recovered had to replace stereo, lower dash panel that they had busted out ripping the stereo out, steering column that they had busted into and started the car w/ a screw driver, and patch up the door skin where they had popped the lock cylinder on the drivers door.
5) various $50-$100 repairs(sensor here, motor mount there)
6) this one at least partly my fault- brakes never thought about 'em untill the wear tabs started chirping, and even then didn't do anything untill i couldn't drown it out w/ the stereo. so when i took it in, not only did it need new brakes all around, but the flexi brake lines up front were pretty rotten, and had to be replaced, and the front struts were shot and needed replacing as well. (totaled over $900)
7)about 120k mi,(maybe mid oct.99) the Timing belt broke. had it replaced($600), but the damage had been done. the oil passages had been blocked, and with in 500mi the engine sounded like a meat grinder.
rebuilt(Jasper) engine installed($2500)
8)Shortly there after, i was clowning around in the college parking lot, and heard/felt a loud BANG!! from under the hood. drove ok, so i ignored it. after a bit, it started chattering/bucking when you first take off from a stop, unless you reallly grannied it. then heading home from work on christmas eve morning, it just would go forward no more. I was able to throw it in reverse, and get into the driveway of a couple from my parents church. after i got it towed to the trusted local trans shop, turns out i had some how snapped the drive band...oops... tranny rebuild ($2000)
9) clutch in the power antenna motor burns out (while i'm on crutches, and in in no position to tear the wheel well apart to try and fix it) causing the antenna motor to run constantly (even with the key out). I discover pulling the radio fuse kills the circuit, so i do that EVERYTIME i turn the car off...after my legs healed up, i bought a "universal" power antenna kit. will NOT fit where i need it to.(darn GM and their structural supports for the fenders!)so just replace it with a standard fixed mast antenna.
10)CAT self destructed, and heat sheild rattled constantly.
solution: a) remove heat shield(just the downward facing part that was doing the rattling) b) later on (since i didn't feel like starting grass fires @ the fairgrounds-"lawn parking"- actually put a universal cat on (~$200)
11) NOT MY FAULT!! - went to the local(corp. owned) goodyear shop to get some new tires. while I'm waiting, i hear this horrendous crash sound. the tech had mistaken the cars second (LEFT)accelerator(grandpa's right leg was amputated) for a clutch or something...slammed the car into the columns between the outer bay doors, right in the center of the Rad, cracking it in 1/2, and bending the frame/unibody...
they paid MY body shop to repair the damage, but for some reason "couldn't" rent me a car, however they could reimburse me for the rental when the repairs were completed. (2 mo, and $900 in rental charges later...)
12)some where in there the rear gas struts (car had "air level ride") went out. i never replaced them ,when i sold it it looked like it was kinda squatting..
13) some idiot tried to roll down the rear drivers side window during the winter months...it popped, and went down about an inch, never to move again...(duct tape to the rescue!)
14) summer 2001, as i started shopping for a new car,the ac started leaking freon (r-12) (14yrs in the rust belt.. not unexpected really)
when i sold it, with 140k mi on the odometer, EVERYTHING forward of the "A" Pillar was less than 2 yrs old
about 20k on rebuilt engine @ trans.
between my dad, and Goodyear, around $10k had been put into the car, that i could only sell for book value ($2000)
(to be fair it still needed a couple grand in repairs...Rear struts, ac leak, window motors, windshield seal,etc.)
I still have a pair of fog lamps i bought for that car, and never got around to installing....