Ha ha, fun thread! My first car that I bought with my own money was a 65 Ford Country Sedan: 6 cyl. three on the tree. Lived in the country for a year after graduating. Never got stuck in 3 foot drifts (not enough power to spin the wheels!).
Now my 01 Boxster S pleases me all to hell! Bought it on a whim in California and imported it to Montreal, Canada. (I'm still working on my road movie, coming soon to Vimeo!)
Great fun doing upgrades in my junky garage, and yeah, it is a bit needy, but better spend money on that than fixing the roof!