In 1966 I was fresh back from Vietnam, selling cars and took a '66 427 Shelby Cobra in trade. My common sense said I couldn't afford it-I'd just wreck it-I'd lose my license shortly-etc-etc.
I've kicked myself hard for 50 years for no getting it and being smart enough to just put it in storage. I'd be a very happy wealthy man ($5Million) today if I had just followed my heart instead on common sense.
In retrospect, my son & I built a Factory Five Racing Cobra kit and we both had a blast with that car. No arrests, no convictions.

 

I'd rather not think about it ......................

 

had the opportunity back in 07' to buy a 08' Honda Civic Mugen SI that was strangely built up with SPOON parts, so it was a Honda Civic Mugen Spoon SI, a dealer had built it up as a promotional piece for there dealership, wasn't able to convince the wife why it was so awesome (or why it was stickered at $38k)

 

I had the chance to buy a low miles, Phoenix Yellow Integra Type-R. It was extremely clean and at the time was pretty inexpensive. Due to having a young family I needed something with 4 doors that could handle car seats. Ended up with a brand new Mazda3 instead.

Worst car ever was my 2003 Audi A4. What a turd.

 

Most of the cars I regret not getting were cars I could not afford at the time anyway. For instance, I didn't have the ~$200K it would have cost to buy a real 550A Spyder around the time I fell in love with them. (They're several mil now if you can find them!)

I do kind of regret not trying to buy the Tatra 605 that BringATrailer sold about a year ago. I don't know where the heck I would have put it, but it sure would have been cool!

 

1969 Plymouth roadrunner. 440 6pack/ pistol grip 4sp. $1400.00. The engine was slathered with blue RTV, so I walked away.

Several mentions of 1st gen Z cars here. I still have a 72 240, and a 76 280 with a 408ci SBC/700r. Street legal, but mostly used for bracket racing.

 

Here is a pic of a 68 GTB and GTS I turned down because of the first Arab Oil Embargo. I had put down 3K for a total due of 8K on the 330 GTS, but didn't want the payments when we may be rationed for who knows how long. Most guys in those days were school getting their masters or were in Viet Nam.

 

I pretty much buy what I want, but while we were living in Belize, my wife stopped me a lot, lol. See, I love old Defenders and have a burning desire to rescue each and everyone I seen in Belize. The old guy only wanted $1,500, it ran good but looked rough, the way I like them. Was going to import it back. One day I shall prevail, lol.

Now talking about the cars I should have not sold.

1988 BMW M3
1983 911 SC Cab
1987 Mercedes 190TD and 2.3 Cosworth
1988 16V Scirocco
2004 Land Rover Discovery Expedition Edition
1994 Land Cruiser Expedition Build

and the list goes on!

 

Not one but two 70 Olds W30 442. One I bought a built but wrecked W30 with frame damage ended up reselling it back to the owner for dirt cheap. Years later I was given a 442 by showing interest in the car as it sat in a church for weeks. Crash it after a year ended up selling it cause I couldn't afford to repair it.

 

Local dealer had a brand new blue w/white striped 2005 Ford GT at list plus $10K. I knew they were making at least $20k at the sticker price which I offered but they refused. Hindsight is always clearer than foresight.

 

anywhere between 15-20 years ago there was plenty of opportunity to buy older air cooled porsche's, I regret not buying one now

 

In 1991 had a 1978 RX-3 3B in Near Mint (needed new interior, body was immaculate) in my hands ready to trade for my 1981 Datsun B210 Station Wagon 1.2 liter engine. I, instead, Sold the Datsun and bought a 1983 RX-7, 4b, G body, which was a low flying plane when we were done with it, but it always stuck with me about no buying that RX-3

 

When I got out of highschool (2009) I had the chance to buy a MINT E30 M3 for 10k. At the time I was just starting to look into Euros, had just bought a MK4 GTI and thought 10k was too much for me to pay for a 1988 car of any kind. I have since owned a few E30s and regret not buying that car (not only for the driving experience, but they have gone up an insane amount in price!)

 

ouch

 

Back in '70 there was a XK120 roadster in Ivory for sale, needed some work, they were asking $700 or $800. I had a lot of other responsibilities at the time and had to let it go. The idea of that Queen Mother not parked in my garage still hurts a little. Especially when I see one. I did enjoy a '63 E Type for a few years though...even the occasional smoke from the starter.

 

A gray import Seat Fura Crono last year that turned up locally for $4k. I had the money, but was in the middle of a major work project, and didn't have any free time to go check it out. It's a car that's so ugly, that it has character.

I doubt there's another one of those in the US, or that another one will make it.

 

A good buddy of mine back in the early 90's had an affinity for convertible classic Muscle Cars. He was the money guy, I was the mechanic who went along to pick the car apart, leaving him to make a low offer. He always had the cash. We bought many cars, flipped them all for profit, a few times making 46 cents or so, many times making a couple grand. We always had fun, and he accounted for every cent spent, including gas money and advertising. Everything from a 1968 Plymouth Sports Satellite convertible in fire engine red, with a 383, to it's "parts car", a 1968 Plymouth Sports Satellite hardtop. We made more money on the parts car when all was said and done. LOL. We had a few Cutlasses, like a 1971 Supreme SX convertible with a 455, T400, silver with black Rallye stripes, a 1970 S convertible in black and white, with the W-30 option, and that cool hood with the scoops. I would have taken any of those cars back in the day, but they were "for-profit" rides. I really don't know how much money we made, but that wasn't really the point, after all. I made some money fixing stuff, getting them ready for sale, sure. But, mostly, we had FUN! It was the thrill of the chase. His personal ride was a 1974 Caprice Convertible, with a 454. I made some money fixing that big old boat as well, and I would say THAT is the one I miss the most. Or maybe the 71 Cutlass Supreme SX convertible in silver and black. Those old big-blocks could really push those big rides along very well. Fuel mileage be damned, full speed ahead!

 

When I was shopping for a GTO I first drive a 6spd version, but the dealer wanted 1-2k more than I wanted to pay for it. Found another that was auto for the price I wanted, and thought ehhh...the SO can drive it too (she doesn't drive manual), and it feels ok.

My overall experience with that car was lackluster. I kinda wonder if I went with the 6spd if I would have enjoyed the car.

 

Very interesting and fun thread. Like a previous poster noted, the cars I regret not buying are the ones I couldn't have afforded at the time anyway. It blew my mind when, at 18 years old in 1984, I saw a new Toyota with a sticker for $18,000! Maybe some of you will remember that 18k was a lot for a Toyota back then. It was the Supra. I loved that car. But I guess you could have called it cheap since a 911 Turbo was around 70k at the time also. 1985 is when I began my 20 years of service and I had a couple fun rides, but my biggest regret would have been not entering the German car market at the time. After all, I was single up till 1997, but the BMWs and Mercs seemed rather dull and stodgy at the time...just Taxis at the Bahnhoff and the Talons, GTIs and Eclipses were fun and the better bargain until.... they showed their age a couple years later and the rattles would set in. Now that I'm a little older and have discovered that a husband is only a two-syllable word for tool or mule, I regret not getting one of those early to mid 90's BMW or Benz. I could still have it today or could have made it much easier to trade up as the newer generations came along. Look, you can't even buy a new MB with a normal person transmission and you'll never find a manual BMW on a car lot in the U.S. either. I appreciate build and material quality now and am still hesitant about getting a Clubman. Being the "tool," if I'm ever fortunate enough to buy a new car again, I need to hit the target on the quality/longevity thing. Ohhhhh...I have my regrets...but is it really about cars?

 

Probably my biggest regret is the '69 Z28.

Guy I worked with had just finished rebuilding the engine and was taking it on a shakedown. Pulled off on the hard shoulder and was side swiped by a semi (lorry for those on the other side of the pond :D). Trucking company paid for new panels and paint (bright red w/ black accents on fender and hood vents). He got it put back together and said he was just gonna sell it. I asked how much and he said "Eh, you're a friend. Probably $2500 for you."
I was in college and $2500 just as well as had an extra zero at the end, but I wish to this day.

 

Only seven years ago, a car guy who lived in my area found out he had cancer and offered me not one, but two classic 911's for $40k. One was an 85 930 turbo with 75000 miles and perfect everything, and the other was a 87 911 coupe. He offered me a deal because we had just adopted two kids and I had just sold my 911 to pay attorney fees. He thought, and rightly, that I could sell one and pay off the other. It was like the year before classic 911 prices skyrocketed. That 85 turbo would be worth 150 grand now. Shortly afterward, we bought a Honda Odyssey.

 

I think this story is the most costliest regret so far.

Back in those days who knew some of these vehicles would someday be worth a small fortune?

 

In 1984, a co-worker that was short of cash due to a substance problem, offered me his Bright red 1974 De Tomaso Pantera with 5K miles for a mere $10K.
I passed on it.
AARRGGHH!!

 

2016 Hellcat. I opted for the scat pack because dealer mark-up was nuts, in the end...a teenage driver would kill the car and delete the negative equity lol.

 

Scat pack?

I sort of regret not getting a E46 M3. But I wouldn't have gotten the Mini if I did.

Now that I have a Jetta as daily, it's more possible to make the weekend car a M3 instead of Mini.