I was perfectly happy driving an older 5-speed Camry until a few years ago, when the transmission started popping out of 5th gear. I had learned a little bit about wrenching, doing brake changes and an ignition system refresh while I owned it. Nothing particularly passion-inspiring about it, and it certainly wasn't a vehicle that I was proud of, but I had many other compelling hobbies that got my money and attention.
At this point, my girlfriend and I were both in the market for cars, and she got it into her head that she would buy a 1970's-era Plymouth station wagon. I pleaded with her to forget it, and to buy something modern. The thought of a carbureted behemoth from malaise Detroit really put me off. I was trying my hardest to get her into Volvo and Focus wagons, but she hated them for their tacky interiors and lack of soul.
When she bought that car, I had an epiphany. I was young! This was the perfect time to make some memories. I shouldn't be buying another appliance, I should be living a life that is worth telling to my kids.
I remember my dad telling me about how he took his Austin-Healy apart, and was unable to put the transmission back together. He told me about his Datsun 510, which rusted so much he used plywood as floorboards, and how he'd leave the key in it so his friends could borrow it. He told me about his beautiful 1950's pickup that got demolished in a freak hail-storm.
I hit the internet, looking for a quirky old car that was small enough for the city, but fun as hell, and could be found with a manual transmission. It came down to a Mercedes Diesel (w115 or w123) versus the BMW E30. The E30 won, based on its absolutely massive cult following, and huge forum presence. Everything I'd ever want to work on was already laid out, parts were plentiful, and help was there if I screwed up.
I bit the bullet, and it's been the best choice I could have made.