In order, with info I remember. This might get long...I like cars. I may have even posted in this thread already but I forget, and there's an addition
90 Lincoln Continental - Smallish for a Lincoln, the typical garbage 3.8L from Ford, very nice ride but nothing but problems. Happy 16th birthday to me. In it's dying days it was overheating and would not shift beyond 2nd gear, or the trans would just completely disengage at random. I ended up donating this one.
90 Cadillac Sedan DeVille - Gorgeous inside and out. Where I developed my love of cars. Bought it off a mechanic friend for I believe $800. Had it painted a metallic gray, bought a hub cap to finish it off and put a thousand dollars into the stereo because thats what high school kids did 20 years ago. Oh I slapped a flowmaster onto it and that 4.5 liter screamed. Such a gem, until the block blew a hole and couldn't stay cool. I was legitimately upset to junk this one.
97 Cadillac DeVille - Sharp looking car, very quiet and soft ride, but pretty dull for a Cadillac. The 32 valve Northstar had plenty of power but I ended up overheating it around 150k. I drove her from Boston to Florida twice though, and slept in the back seat. A nice car but I don't think I'd recommend a Northstar Cadillac to anyone now. I traded this in for the Escape mentioned later.
2006 Toyota Corolla - Hated this car, but was getting 40mpg so hey that's cool. It was totaled after being hit by a plow truck while parked. Insurance dicked me over, which lead to my next purchase
2005 Nissan Sentra - A worse version of the Corolla. Less power. Decreased mpg. Loose steering. I actually forget what I did with it.
2010 Ford Escape - Got married, had a kid, and mom refused to get a van. Liked the look of this one (I like hard lines and boxes) but it was pretty dull, and not all that practical as a grocery getter/family hauler. Traded this one in for...
2012 Dodge Journey - I bought it with 7k miles and it's up to 156k now. Pentastar has very solid power through every gear, third row (which is nice cuz I have 3 kids now) and it's fairly comfortable. Only repairs aside from oil/brakes have been a $12 thermostat, and just recently I did the battery and alternator in the same week, but did that myself so I saved a bit. This car could explode in my driveway today and it will have served me well. It's crazy how reliable this thing has been. Drove it to Florida twice (christ I've driven to Florida too many times) and on the most recent trip, slept in the back with the seats down
2013 Honda Odyssey - Traded the Escape for this back when child 2 and 3 were on the way. Solid power, decent on fuel, very very comfortable and enjoyable driving experience for a van. I drove this down to Hilton Head Island from Boston, alone, and it was the most relaxing 16 hours of all time. I lost this one in the divorce and got the Journey, which has been established to have worked out very well for me
69 Plymouth Barracuda - 340, 3spd reverse manual valve body, 4.10 gears, 8 3/4 rear. Absolutely screwed. Would leave rubber through each gear any time you felt like it. But, my father couldn't drive it, and since we co-owned it, it had to go. I actually sold it to the guy that rebuilt it 20 years ago, and used the cash for...
64 Chevelle Malibu SS - 327, Turbo 350, full restored. My father owned this car years ago, and sold it around 2000 to a friend of his. That friend restored it front to back and sold to another friend who we tracked down...and it's back with us now. This thing is lovely inside and out. I just bought a new bluetooth head unit that I'm gonna jam into the glovey because I don't want to touch the factory radio. I added hand controls so my father can drive it, but we may have to add a tilt wheel column too.
So it all worked out that the Cuda and the Chevelle both took 20 year breaks and then ended up back in the driveways they always belonged.