My first was a '57 2 door hardtop, bought for $175 in 1972. 4 barrel Power Pack with a PowerGlide.
It didn't run, so I used a tow bar hooked up to a Greenbrier van to get it home.
First I installed a 265 bored out to standard 283 with 11.5 to 1 popup pistons and a 30/30 cam and solid lifters, with stock power pack heads, and a Borg Warner T-10 4 speed.
Since I didn't keep the main caps and rod caps in order, so it developed a rod knock.
I had the radiator checked at a shop, but they only checked for leaks -- not for flow.
We took it 900 miles into Mexico from Oakland, CA for a vacation, sometimes running over 90 mph.
On the way back into the U.S., we heard a scraping coming from the right front wheel.
After getting through the border, I pulled off to the side and took the wheel and drum off to take a look.
The ball bearings fell out into the sand -- the bearing cage was toast.
After using spare grease from the dust cap to hold them into place, we limped it 20+ miles into the first town and parked in a car parts parking lot until they opened.
With a hammer and screwdriver, I pounded out the ball bearing race and installed the new Timken roller bearing.
A few miles later in LA at my brother's house, the right rear wheel bearing was leaking badly. Off to the machine shop to press on a new bearing.
On the grapevine (long uphill grade on I-5 North of LA), the heater was on to cool the engine (since the radiator wouldn't), but only cold air came out of the heater.
At the top, we stopped, and the engine seized. After some hours to let it cool, it started again, and we drove it home, running badly and using way more gas than it should.
At home, I pulled the heads and saw the head gasket was melted between two cylinders on the passenger side.
Later on, I made another mistake by installing a 427 from a corvette that a friend had.
For some reason, I used a 3 speed from my cousin's '56 for a few weeks, until the 427 ground it up. And I spun two sets of spider gears in the rear end.
Sold it after I got married for $600. A few weeks later, the buyer came by to yell at me because the rear shackle tore the frame where the shackle was mounted.
The things we do when we're young and stupid...
I probably bought, fixed and sold six '57s and a dozen other cars in those years.
We used to read the want ads and go look at cars on weekends and offer 10% of the asking price.
More than a few called us back after no one else wanted to buy their car.
One '57 we bought for $15 that wouldn't run. After signing the paperwork, we cleaned the battery terminals, jump started the car and drove it away.
The seller was very angry when she saw that. It had an few inches of bondo in multiple locations, IIRC.
We cut out the roof with a torch and drove it around as a convertible for a while before stripping it of useful parts.
I must now apologize for doing so much damage to that car....