Originally inspired by this Doc Searls post and published in 2007. Updated in 2021 because why the hell not.
1989 Plymouth Laser - The twin to the Mitsubishi Eclipse. I bought this upon graduating from college in 89 and getting my first real job. By all accounts it should have been a solid car. I apparently bought one that went down the assembly line the day before a long weekend, or maybe on the first day of hunting season. It was a lemon with electrical gremlins that I never did figure out. I had to make sure I always parked it pointing downhill, or at least on a flat surface as it frequently needed to be push started. The real advantage of it though was that the back seat was only useful for storing a bag of groceries, so it was functionally a two-seater and kept me from having driving duties back in my bar hopping in Buckhead days.
1991 and 1992 Mazda Protege - My wife had a 91 Protege, and I was so impressed with it that I dumped the Laser and bought one myself. It was the base model with a stick shift. It was a great car that gave me no troubles at all. She had the luxury version with power moon roof, power windows and all that.
1996 Isuzu Rodeo - With the arrival of a child in 1994 we quickly realized that life as a two sub-compact family was less than convenient. When we bought the Rodeo I traded in my Mazda and took Michelle's 91 Protege as my daily driver. The Rodeo was a great vehicle. We had no problems with it for 4 years.
1997 Mazda 626 - Right after Y2K the transmission stated to act up in the 91 Protege. Since I had already rebuilt the transmission once about 3 years previous, this seemed like a good time to bail. 150K miles out of a 4 cylinder engine is nothing to be ashamed of. I replaced it with a 97 Mazda 626 with 36K miles on it and we drove that thing until it had about 205K miles on it in 2014, and was literally held together with duct tape, and the trunk only opened by using a screwdriver. We gave it to Goodwill.
2001 Mazda MPV - As a two child family we found the constant lifting of small kids up and down into an SUV to be a royal PITA. In early 2000 we went to the DC Auto Show for a day out and found the MPV there. We wanted the fold down seats of the Honda minivan but didn't have Honda money. The MPV provided a lot of the same features for far less. Reviewers always claimed that V6 engine was under powered but it never bothered us. It's a freaking minivan! I don't think it ever saw a shop for anything other than routine maintenance.
2005 Dodge Durango- With the addition of a horse to the family, we needed something capable of pulling a horse trailer. The MPV obviously wasn't going to do it. I considered keeping the minivan and getting a beater truck for a tow vehicle, but my wife vetoed that plan. The truck was coming off a one year corporate lease, and I got it for about 50% of the list on a new truck. It's the most loaded vehicle we've ever owned. It had every single option available on a 2005 Durango. The HEMI is amazing. When towing 4000 lbs of horse and trailer at 60 mph the RPMs were comfortably under 2000. Unfortunately the mileage when towing was not-so comfortably under 10 mph.
2004 Dodge Durango - The 05 Durango was totaled in an accident, nobody was seriously hurt. I got about a $15k check from the insurance company and spent $8000 on the 2004 in a more modest trim level and with Dodge's standard 8-cylinder engine. My wife was not amused but my bank account was. It served us well as the tow vehicle until our daughter went away to college. We gave it to our older son already in college at that time and retired the Green Menace (the 626).
2001 Park Avenue - In early 2012 my mother made me an offer I couldn't refuse on a 2001 Park Avenue. We had 3 cars and two kids driving in the house, with both parents commuting, so a 4th car was actually useful.
2011 Toyota Corolla I dropped the Durango off for its annual safety inspection and my mechanic called and said I could either give him $2000 to do a bunch of repairs or trade it in immediately. He recommended the trade-in option. This was Michelle's daily driver until 2020, and we never did anything other than routine maintenance on it.
2012 Toyota Camry - I got that same call from my mechanic about the Park Avenue - it was going to be $2000 to pass inspection and in fact it was likely to catastrophically overheat the next time I drove it. So I traded it for the Camry in 2016 and it's still my daily driver. I put 3000 miles on it this year.
2012 Ford Edge - In Spring 2020, looking at the cancellation of weeks of summer plans due to the pandemic, we decided to pivot and buy the camper I had always dreamed of but could never justify when our weekends were filled with fencing tournaments and horse shows. Our Toyotas certainly weren't going to tow anything useful so we traded Michelle's Corolla for the Edge and we spent 30 night this summer and fall camping.