Like many of you, I've had plenty of experience with sketchy rides. Here are some of the sketchiest:
1987 Mercury Cougar XR7: I bought it for $250 from the dealer my sister worked at, because it was cheaper than getting a new gas tank for my '64 Skylark at the time. It had been hit on the rear driver's quarter, but it ran and drove home. Interior was nasty, windows didn't roll down, it was filled with trash, and it would do this weird thing in reverse like it had stripped gears. I pulled an amazing assortment of crap out of the engine bay including a fork, knife, and spoon, 2 non-functional alarm systems, about 75ft of wire that went to nothing, various rags and towels, and a Chips Ahoy box propped under the headlight. I only had it for a few months before the transmission lunched itself, and the dealer sold me yet another 1987 Cougar XR7 that I had slightly better luck with.
1979 Trans Am: Yep, this one. When I bought it, it was replacing my 1989 Maxima SE as a daily driver. That was a mistake. A week after I bought it, I found that most of the exhaust manifold bolts were snapped when I tried installing headers, so I had to pull the heads to have them drilled and tapped. Then, after doing a tune-up, it caught fire and nearly burned to the ground (my fault, put the incorrect ignition module in it). There were plenty of former owner hacks I had to fix, and after just one day trying to drive it to school and having it barely make it there and back, I gave up and got a different DD. It's been relegated to Project Car Hell ever since.
1979 Dodge Power Wagon: Also something I currently own. I knew what I was getting into when I bought it, and it's come a long way since, but there's still plenty of sketchiness that needs fixing. The electrical system had more scotch locks, wire nuts, and bare wires than a Radio Shack had in stock circa 1985. Most of the hoses were dry rotted and cracked, the fuel feed line had about 12 splices in it and no clamps, the filler neck was held on by grease, and it leaked enough oil to make it onto an EPA watch list. The thing was basically a rolling Superfund Site. It's a lot better now.
BONUS! NOT EVEN MINE! 1995 Chevrolet Suburban: Back in 2010, my friend bought a 1995 Suburban from another friend for $1000 to use as a tow pig and dump runner. It was 2wd, had the 350, and plenty of rust, but it ran and drove and the trans had been replaced at some point. We took it up to the Canadian border on a rafting trip, and it did well until the end of the trip when it started running funny, so he threw a tune up at it. About a month later, we hooked up a trailer and attempted to drag a Miata to the Challenge to go along with our Jeep XJ-R. We got to about CT and it started running worse than ever. After stopping for an hour at a parts store, we threw a bunch of sensors at it, but it didn't care. After getting back on the road, it would give us full throttle and then nothing, no matter the pedal input, and that came in waves. After some internet sleuthing, someone said to unplug the O2 sensor, and we got it running closer to normal. And that doesn't even cover the rest of the issues! The steering was super loose, so towing at highway speeds was a challenge.
Then there were the brakes.
On day one of the Challenge, on the way back to the hotel, we stopped for beer. Our race car was street legal, so we left the trailer at the hotel and had both cars with us. I get in after buying beer and immediately pop a brake line. We just happened to stop within walking distance of a parts store, and were able to cobble together a brake line, but we missed part of the day 1 festivities at the hotel. Later that night, after a few beers, we decided to get stupid and cobble together a turbo swap on the XJ-R in the hotel parking lot, which ended up being a life-changing event!
Oh, but the Suburban wasn't done with us yet! It got a flat tire and one of the calipers locked up after blowing out a seal since now it was getting consistent line pressure with the new line. We also had to plug the flat tire on the vehicle because the wheel was seized to the hub and none of the tricks worked to get it off. We eventually made it back to MA, but yeah, that was the sketchiest tow rig I've ever piloted by far.