2000 Audi A6 2.7T with the 6 speed manual. It was a blast for back roads and on the highway, but the check engine light was always on (even with a Bosch certified tech/VAG guru working on the car) and the impending doom of replacing everything was enough that I got rid of it. When I got my F150, I doubled my car loan and lost 10 mpg, and I think I doing better financially now. 
'98 Audi A4 Avant 2.8Q. Gorgeous car. Drove beautifully. But after it blew up on me, I never trusted it again and doubt I'll ever really trust another Audi.
My old Spit 6. Take everything that's fun about a Spitfire and then kill the handling... leaving you with a loud, twitchy car that cruises at 80 mph w/o trying... However, I still have a want for another Spitfire of my own to drive/modify - but a 4-banger, though.
My E30 (although I still have it). It's simply not as much fun to drive as I thought it would be. But I guess with a Spitfire, two MINI's and a 1800ES in the fleet, my opinion has been jaded.
I've never owned a Beetle, nor had any desire to... To me, they're like dogs: Fun to play with now and then, but as long as someone else has to deal with the walking and picking up poo...
1977 Cadillac Sedan Deville, 425 V8, Yellow exterior, yellow plaid interior, more than a gallon of body filler where what I can only assume was a semi truck hit the door causing a bit of a ding. 6mpg. City, highway, driven hard, driven casually, didn't matter, 6mpg, granted this was before gas hit $1. Still, tons of torque, tons of metal, fun to slosh around in. Was I glad to see it go? Yes. Do I want another? Hell no.
1998 Ford Contour SE V6 5spd. The car was fun to drive, handled great for what it was, had good acceleration for the time, actually had decent parts availability and didn't look terrible.
The bad part was that any little thing the car needed was a gigantic pain in the ass to do, from struts to brakes to wheel bearings, to cleaning out the massive quantity of flaky carbon crap from the overly complicated dual runner intake manifold. Then the CAT failed, then the ABS pump got mucked up and started letting the rear wheels lock up, then the... Well really just alot of abuse at the hand of a highschool/college student and his friends happened. Fun car to drive though.
2001 Honda Civic Coupe, It was a fine car and took nothing from me but gas money and regular maintenance for almost 100k miles (sold with ~130k), just don't park a Civic long term on the street in Chicago and expect all of the parts to remain attached to the car. There are just too many people willing to buy used Honda parts from craigslist.
Most of my vehicles have stayed relatively stock when I got them and later on the knowledge of how and where to get all the good upgrades can be nice. That said I think I would rather have a new platform to play with each time I move to a new car. Buying at the right time (bottom of depreciation curve) gets a lot of bang for the buck.
I've had over 20 cars... and there is one that ALWAYS pops to the head of the list when I'm asked this question.....
1991 Peugeot 405 Mi16
Miata
Corrado VR6. A low-volume VW, produced at a time when VW had to operate their plants at 98% capacity just to break even, assuming the cars sold at MSRP. Nuff said?
I had a '98 Jetta with the shoe-box 2.0L and a 5 speed. I learned how to drive stick (legaly) on that car, handbrake fell easily to hand, blizzaks made snow easy. I could also fit my bike in the trunk with the rear seats folded down. It also did well on the daily race to lunch in high school. On the other hand, I had to fight rust, one window stopped working, one fell into the door (in february) the lights barely worked without hitting them, and the beeping was annoying. I also had to replace a clutch, ignition coil, plug wires, distributor/cap, and if i followed a truck in a blizzard the gas line would freeze and it would die. I only had the thing for 2 years.
Now a car I don't ever plan on selling is my '87 econoline. That one has never gone wrong, and i can fit a lot more than a bike in there!
OTOH, the jetta's 30mpg is looking pretty good now that i only have cars that get under 20mpg.
'93 VW Corrado VR6. Beautiful car, nice fit and finish, orgasmic VR6 exhaust sound.
Incredibly unreliable, incredibly expensive parts that were corrado only. $125 door handles!
I loved my 323 GTX..... nuff said, really.
'65 Mustang Fastback. Owned one for 16 years. I tried to make it handle. I failed.
97 Audi A4 1.8tq, loved it. Just didn't like fixing it. When it was in perfect working shape I loved it. Always seemed to need a wheel bearing, control arm or a set of brakes.
I wouldn't buy my '73 Capri again because of the rust. I still own it but it hasn't moved in many years, not sure how to get rid of it. My '88 626 Turbo was an excellent car, wouldn't buy one again because of the weak transmission. My '64 Plymouth Savoy was cool, you shifted it with pushbuttons! Factory radio delete and a steering wheel more at home to a bus! But I didn't own it very long; I would buy another like it today if they didn't sell for absolutely stupid money because of goons putting non-correct engines in them and building their completely stupid drag cars out of them. I'm bitter.
My current car is a total appliance boredom machine and I've had it the longest.
1989 Merkur XR4Ti.
I always wanted one and found a gorgeous 19k mile example that was pristine. I babied it, never driving it in the rain, cleaning it meticulously including the undercarriage and suspension. It won multiple awards at the Ford Show at Carlisle and was a so much fun driving it on a nice day. It turned heads everywhere because it was so clean and well kept but....
All kinds of E36 M3 broke, even when just sitting in the garage. I got so tired of locating parts and fixing it myself that I sold it for a pittance. Took a major bath on that car, worse than any other that I've owned. I love looking at pictures of it, diecasts, and the trophies that it won but I'd never want it back in my driveway again.
Ironically, I traded my 1975 Datsun 280Z in on the Merkur and after a few years I eventually saw the Z up for sale again and bought it back in a deplorable and well abused state and I could not be happier. I still have the 280Z after many years and many other cars that have come and gone and I doubt I'll ever sell it.
The 1986 Toyota Cressida I had fits this. I love the Japanese styling, its reliability. But it came down to the fact that there is no aftermarket support, and the thing drank gas without being very fast. I am glad I did get the chance to have one for a few years but I really don't have any need for another one.
1968 Datsun Roadster with the 2-liter. The only car that I sooo lost my temper I threw the exhaust header across the yard. Loved driving it, HATED working on it, as it was hard to find parts for it, the parts that existed were expensive, and the fact that this was before Datsun/Nissan figured out how to make things servicable. Like, you can't get the starter out unless you removed the header, which you can't get out unless you removed the starter. Love the memory of driving it but don't miss it for a second. Kinda like dating a supermodel who's a head case, or so I'd imagine.
Had half a dozen Datsun 1200s in various states of tune. Still miss those and wouldn't mind having one again - 35 mpg would be nice.
12 years was a good run. What a great car. But having more-or-less replaced it with an E30 I'd never go back.
Over 20 years with this one, and several more prior to it. I just got burned out on them.
I would someday consider another Subaru Impreza (this time a 2.5RS) and I'd be hard pressed to refuse a nice original Mk1 Ford Fiesta. Other than that...I need not repeat past mistakes.
I've owned two 1st generation Rx-7s - loved them but variety is the spice of life and no need to own a third when there are tons of good options out there.
VWs. Any VW. I've owned 3, an 83 GTI, 85 Cabrio, and now an 04 GTI 1.8t. I like driving them, I want to like them, but they are just really unreliable, and difficult to work on.
'92 Saab C900S sedan. Great little daily, not awful to work on, comfy and reliable, but... I can't say as I'd seek one out again.
XR4Ti. The name is explanation enough.
My 88 Lincoln Mark VII LSC is one I probably wont buy again.
turbojunker wrote: XR4Ti. The name is explanation enough.
It was an interesting car...
X = frame?
R = RWD?
4 Cylinder
Turbo
Injected
87 turbo2 rx7. It was amazing for a stock car, didn't give me terrible mileage, never left me stranded, ran a 14.6 in the 1/4. I think if I were to revisit the rotary I'd want it in either a FD, a GSL-SE, corvette, or some kit car/locost. The FC chassis is pretty awesome and makes a great daily driver but I'd rather drive something with more mpg for a daily or a lighter/more exciting chassis for a toy.
NA MKI MR2. Fun with relatively little power thanks to a lightweight mid engine chassis but I'm still looking for one car that can do everything and a 2 seater without a hatchback doesn't seem practical. I am hooked though and could see going back with a turbo 4agze in a satin black mki with box flares for a group b knock-off car.
This post made me think of something I never contemplated, but could you put a rotary in a MKI MR2? I don't know have enough transmission wizardry to know the answer.
I owned an 84 Audi 4000S and, later, an 85 4000S quattro. Reliable cars and I liked the styling, but something about the driving experience just never quite rubbed me the right way.
On another note, before I even opened this thread, I was wondering if a BMW 2002 inspired it. I've owned four of them (and currently own one) and can think of no other car that I've more intensely loved or hated. All that said, it's the car I keep coming back to.
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