After the Special quit, the first car I ever bought was a '65 Ford Galaxy 500 with a 289 V-8. (While shopping for cars, I looked at a '66 Mercury Comet, but when my dad opened the hood and saw the 427 V-8, he said " No way, You'll kill yourself!")
The car was very clean, but used a little oil. After I had owned it for a year, my dad suggested that we do a ring job on it; he'd supervise while I did the work. Unfortunately, right after we started he ended up at the VA hospital for a few weeks. I ended up doing the job alone with just the verbal advice I could get from him on visits.
I goofed up the job. One of the head gaskets leaked water into the oil, and it overheated on my first test drive. It took two attempts to solve the problem, but then it threw a rod (probably from the strain of overheating and running with water contaminated oil).
The car I bought to replace it was a '70 Ford Torino (With a 302 V-8; the same basic engine as the 289, with a different bore and stroke), which I had for a year or so before it started using oil. Spooked by my last attempt at major car repair, I traded it in for a '71 Camaro (350 engine).
The Camaro turned out to be a problem from nearly day one. First, I had to get a new carburator. Then it developed a leak somewhere around the rear window that I never could seal or find, so in rainy weather (which we get a lot of in Oregon) water would collect in the trunk and would soak the carpet behind the driver's seat. The suspension had been lowered to improve handling (It cornered like it was on rails), but this meant that everytime you drove over a speed bump it bottomed out, which tore a hole in the exhaust system. I kept having to patch it. Then it cracked a head, which cost me $400 to get fixed. Then it started having starter problems. You'd go out, turn the key and... Nothing. I replaced the solenoid a few times and even the entire starter and it would still suddenly decide that it wasn't going to turn over. After it stranded me in front of a convienience store 45 miles from home, I had had enough. I had a friend who lived in the area sell it for me.
Meanwhile, I was without wheels (Which I needed to get to and from work), short of cash, and had no established credit, so I bought the first car I could afford, a '70 AMC Ambassador.
I kept the Ambassador until I got married and we bought the first brand new car I had ever owned, a 1984 Honda CRX.