Number: 1
Name: Jessica
Make / Model: Ford Escort (wagon)
Year: 1994
Owned: 2005-2009
Price paid: $2600
Reason for parting with: Accident damage / rust damage.
Jessica was my first car, and I still have fond memories of her. But she had the misfortune to be a northern car, and suffered numerous problems with rust, often in completely unexpected places... like the alternator, and the gas struts holding up the cargo hatch. Ultimately, I rear-ended someone who decided that it was a grand idea to come to a complete stop in the middle of a highway. The damage was repairable, but at the cost ($1300) I decided the money would be better spent on buying a southern car completely without rust issues.
Number: 2
Name: Cassandra
Make / Model: Ford Escort (wagon)
Year: 1994
Owned: 2009-2011
Price paid: $2300
Reason for parting with: Second engine failure.
Cassandra had a thing for betraying my trust. With her, it was always something unexpected. Like the time I drove from Florida to Vermont, and didn't see the check engine light until I was on a Vermont back road, and got ripped off by a local shady mechanic. I wanted to trust her, but things just kept happening. Blew an engine after less than 10k of ownership, and various lesser things with alarming regularity. I must have put almost twice what I paid for the car into it over those two years of ownership. My final impression after she blew a head gasket and ruined her second engine? No more domestic cars.
Number: 3
Name: Lisa
Make / Model: Volvo 960
Year: 1992
Owned: 2011-2012
Price paid: $998
Reason for parting with: Bought the Mercedes.
Lisa is currently what I'm driving. A strong old Swedish brick, I got her cheap as dirt, and she's behaved herself very well. Not requiring anything more than routine wear and tear work and maintenance (some of it overdue) to be roadworthy in a 20 year old car for less than $1,000 impresses me. And at 187k, I trust her more than I was trusting Cassandra for the last year. I'll be sorry to see her go, and hope I can find someone who'll appreciate how solid a car she is, if a little rough around the edges.
Number: 4
Name: Ruhe (preliminary, subject to change. German for "Serenity")
Make / Model: Mercedes-Benz 300TD (euro spec)
Year: 1984
Owned: 2012-∞
Price paid: $3600
Reason for parting with: Over my dead body.
Everything I've ever wanted in a car. A reputation for extreme mechanical reliability and durability, a body with some fucking CLASS (chrome trim is godly), and an engine tolerant and flexible when it comes to biofuels. She's a fixer-upper for sure, but if I put the money in, pretty much anyone who knows these cars says that it's not even halfway through it's usable lifespan, and that's the conservative estimate. Frankly, the old girl will probably outlast me.