My first was a '69 Caddy Sedan DeVille I bought for $125. I spent a thousand on tires, and alignment, and maintenance items long overdue, before I could drive it. I did not soup it up, but after the initial thousand, it provided trouble-free driving from age 16 to my child's birth after college and a good career start. I think I owned and drove it regularly for more than 10 years. It went away as a demo-derby car! Did well as I recall, but I could not bring myself to go watch it's demise! I loved that car. It could get me and 7 friends anywhere in "style", and all at 8mpg.The first car I wanted to buy was a Black 58 Thunderbird that was for sale at a gas station that was owned by my friend's uncle for $500. I was 16 and my father would not allow me to buy it!
When I was 18 I purchased my first car, a Black 67 Mustang Fastback with a 289 - 4 speed. I mistakenly purchased it at night. It needed new brakes in all 4 corners (had to borrow the money to do them) and there was a trail of oil smoke in back of it, so I learned how to rebuild a car engine (we had previously monkeyed with lawn mower engines). I sent the heads out to be done and did rings and rod bearings w/o removing the block from the car.
A friend of mine still talks about seeing sparks flying off the crank as I honed the cylinders with my drill.
Added a 600 Holley and dual exhaust (thrush mufflers - LOUD), and I never got beat by another 289 or 283 (and there were lots of them out there at the time).
I could even beat my good friends 69 Z-28 to 60 (after that he pulled away from me), but it drove him crazy that I could do that!
I think if I put a 289 Hi per cam in it and headers he would have been in trouble! (Like Shelby did with the GT-350s).