What car, truck or motorcycle do you regret NOT buying?

In 2018, I passed on an 2014 Audi S5, still seen in some dictionaries next to the word "creampuff". Fully loaded, CPO, white with the scarce Magma Red interior, a smidge over 12K on the odo. Foolishly, I went to another dealer that had a 2013 RS5. Fully loaded, 38K, but... the 4.2L V8. 450HP of gas-swilling, tire-shredding AWD goodness. The engine sound was (mostly) worth it by itself.
 
I was 17 and looking for a cool car. My money was burning a hole in my pocket. I lusted for a Jaguar XKE and found one for $2000. It was either the Jag or an Austin Healy 3000. Two of the most gorgeous cars on earth.

Dad was a wise man and owned an auto repair shop. He knew I'd be wrenching on those cars and convinced me to run away fast. Well, I ran to a '69 GTO. Hah! I wrenched a lot on that one too. The car was great fun provided you didn't expect to stop or turn.

I don't really miss he old Goat, but every time I see an XKE or a 3000 my heart skips a beat. If only . . . .

Yeah, the woulda, coulda, shoulda line of thinking.
 
I rode Japanese sport bikes in the '70s and '80s, and bought my first Beemer, a restored 1976 R90s, in 1992. A 1995 K75s was next, followed by my current ride, a 2013 R1200R. All great machines, to be sure, but...

The one BMW I've lusted after for years is an R100RS. When they were first introduced in 1977, I couldn't begin to afford one...and now that I could afford to buy one, my deteriorated spine probably wouldn't tolerate the riding position...but oh, are they beautiful!
 

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1974. I was 18 and looking to buy my first car. 1969 GTO, 400 4 barrel 4-speed, $400. Unfortunately I was having to go through the Friendly Father Finance Corporation.


I ended up with a '69 Chevy Biscayne, 250 three on the tree, for the same 400. Friendly Father would finance the Chevrolet but he would not finance the goat.
 
I guess I have been pretty lucky! I have never regretted not buying any vehicles. There are some however I have regretted because they were the worst cars I've ever owned.
 
I was a new college graduate in 1989 looking for a new car. I spotted a dark green '68 Mustang at a used car lot and called to ask about it. The guy said it needed "front end work" but it was $1800.
 
About 15 years ago I passed on a '92 Acura NSX with low miles for ~$30k... didn't have room for a garage queen. Today it's probably worth 3 times that price.

About 8-9 years ago, had a line on an early 80's Porsche 911SC in very nice shape for ~$8k. Hesitated a little too long and an acquaintance (serious car vulture) scooped it up. At this point, I'll probably never spend the $$$$ now required to own an air cooled 911.

There are a few others over the years that I would have liked to have owned, or owned again, where prices have moved into the stratosphere, but I've also owned a lot of fun and interesting cars. I also have enough car projects currently to keep me busy well into retirement!
 
Back in the early '60s a local small used car dealer had a Mercedes 300 gull wing coupe. For $3500 asking and no rust. Even though I was wondering just how they ended up with it (what's it hiding?), I tried to get my father to get off my college fund and buy it as an investment. No, really! Didn't happen. Close to that he bought a brand new Dodge Dart for ~$2200.

I grumbled about that off and on for decades until a couple of years ago. Road & Track did an extensive article about the type and I discovered all the stuff about the fuel injection I didn't know back then. Especially how one had to idle the car for several minutes after cold startup to evaporate gasoline that had leaked into the engine oil to avoid bearing failure. Added: also learned the engine was hand assembled and had dry sump lubrication. $$$$$ for repairs.
 
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A used Bullitt edition Mustang that I saw on the lot of the local Oldsmobile Dealer about 9 years ago. Only had 23,000 miles. Looked great and price was reasonable but the Car Fax said it had been repossessed so that gave me pause for concern. Every time I see one now I recall it.
 
Circa 1950 I and another, young, budding car expert had a chance to buy a Mercedes 300 SL Gull wing coupe for $300. It was in a junkyard, in Whitehall, OH. It had a complete, but inoperable engine. Where or how the junkyard owner obtained that rare car wasn't known, but he didn't know what he had.
My fellow car expert, and I were nearly broke at the time, and were trying to find an excuse not to buy that Mercedes. We gazed along the side of the car and gave our expert opinions; That car has been wrecked and repaired; one can see the ripples in the skin. Of course, you could, the skin was hand hammered aluminum from the factory.
I regret not buying that car


Chubbo
 
In 1982 I had the chance to buy a 1964 Porsche 356 Carrera with the correct two-liter four cam engine, for $2,500. I had to pass due to lack of $$. I should have bought the car and dumped the EX instead
 
In the mid 90s I had a customer that had a gorgeous 66 GTO. It had 3 deuces on top of a 389, 4 speed in the console, just almost perfect. The only thing was I detest red cars and it was red as heck It sounded like perfection when cranked. He said I could have it for $6,000. Had the money too. A few days later it was gone. I had to soothe my feelings by buying a 96 Dodge Indianapolis edition Ram which I wish I still had. Oh well I have an 05 GT Mustang that will outrun both of them. That GTO sure sounded sweet but I'm too old to turn wrenches on old cars and every classic I've ever owned was a pain.
 
In the mid 90s I had a customer that had a gorgeous 66 GTO. It had 3 deuces on top of a 389, 4 speed in the console, just almost perfect. The only thing was I detest red cars and it was red as heck It sounded like perfection when cranked. He said I could have it for $6,000. Had the money too. A few days later it was gone. I had to soothe my feelings by buying a 96 Dodge Indianapolis edition Ram which I wish I still had. Oh well I have an 05 GT Mustang that will outrun both of them. That GTO sure sounded sweet but I'm too old to turn wrenches on old cars and every classic I've ever owned was a pain.
Yup,non stop maintenance and $$$
 
A 65 Pontiac Le Mans. With a 326.
My buddies brother hit a fireplug with it and mashed the front clip and a 389 tri-power sitting on the floor, plus a used front clip.
He was asking $500 but that was a lot for me then, back in the late 70's.
 
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