Started with a 1976 Mercury Cougar. Paid about $2500 for it ($2500 too much) It looked good when I bought it...later discovered it was a complete rust bucket. Back then, it got 5 MPG on a good day. This car taught me how to carry a major toolbox and fix cars on the side of the road. Made it last for about 5 years.
I moved to GM, and followed the Cougar with a 1979 Pontiac Sunbird (needed better gas mileage). Then a 1985 Pontiac Grand Am LE fully loaded (first year model). The first "Sunday and cruise only" car followed with a 1989 Pontiac Trans Am.
Switch to Buicks and got a 1984 Buick Riviera T-Type. Now hooked on Turbo Buicks I added a 1982 Turbocharged Grand National, a 1987 Grand National, a 1986 Grand National, another 1987 Grand National, and another turbocharged 1982 Grand National.
Back to Pontiacs and a 2000 SSEi Bonneville, and a 1972 Stutz Blackhawk (it'* Pontiac related as it'* driven by a 1972 Pontiac Grand Prix drivetrain with a 455 4 bbl) and this rounds me back to where I started.....a car that gets 5 MPG on a good day.