Porsche, MG, Lotus
My first 911 was an immaculate, low mileage 1987 Carrera Sport coupe in Diamond Blue Metallic. I ran it for a few years and moved it on for what I had originally paid. Ten years later it would be worth more than treble that!
My second was a 1980 SC that had been converted from targa to cabriolet and was er... less immaculate, so I was happy to backdate it, dropping the weight by 300lb (~150kg), including removing the heating & stereo.
In the wisdom of youth, I thought it perfectly sensible to move on from my first ever car to a 20 year old Lotus Europa. I had to have one. As my only car. With no garage. Or tools. Or mechanical knowledge.
Although restored, the engine hadn't been rebuilt properly so on the first long journey, girlfriend alongside, we came home on a breakdown truck.
The car embodied the 'Lots Of Trouble, Usually Serious' acronym. Petrol running out the bottom of the tank as fast as I tried to fill it was just one amusing episode.
After my experience with the Europa, my next classic was a 1973 MG Midget run as a second car, still with no garage. A few years later I toyed with K-series in a Heritage body rebuild of a further Midget (but didn't complete it), then between Porsches I tried a 1961 Sprite for size.
I adored the first Midget, but tastes change and the cute Sprite just didn't do it for me.