Ive had almost 50 vehicles since I started driving in '80 including off road and watercrafts. I regret selling quite a few of them espcially considering what some of them would be worth today including a 56 Ford Victoria, 67 Chevelle and a 68 LeMans, all worth 10 times now what I sold them for then.
But the cars I regret selling the most were the ones that I was forced to sell or because of what happened to them after I sold them.
(sorry for the crappy old pics, these were scanned from film a long time ago)
My 78 Trans Am - I still lived at home at the time and my parents called it "the devil car". I got in a fair amount of trouble with it including a rebuild using not so legal parts and an NOS system. I spun the main bearings one afternoon doing a burnout. I poured gear oil over the rockers and was able to pawn it off on a used car lot in trade for my first 4x4 blazer.
The first of my Z28's, this one was fast with a destroked 350 (302) and an M21. This was the car I traded the previously mentioned 4x4 blazer for, and ended up running out of state with and it then sat for 2 years with no plates. I finally sold it for parts after swapping the motor into my Chevy Monza "California Special".
The single vehicle I owned the longest up to that point and enjoyed completely was my second 4x4 blazer, this one a '74. Simple 350/350 with bolt on's but I loved this truck. I towed my jet boat and hauled my quads with it, it was a portable camp site for exploring the Sierra-Nevada (lived in the Mojave desert at the time), and was great for desert parties. I regret selling it because I sold it to some "beaners" (no offence to non-beaner mexicans meant) who promptly put small street tires on it, painted the inner fenders silver and covered the interior in velvet "tuck and roll". What a sad death for a great truck.
If I still owned my "Tri-Mag" today it would be Busa powered and a death trap but I still wish I owned it. At the time I had it was powered by a Yamaha Seca 650 Turbo (first turbo production bike ever made I think). Living in the mojave desert and driving a vehicle with no a/c and a lexan windshield just wasnt cutting it. I sold it and bought another Camaro.
Last, but definately NOT least, probably my biggest regret was selling my 68 Camaro SS 396. This was an original big block car with a close ratio M21 and a 12bolt posi rear. It had a near flawless original interior and was a blast to drive. I destroyed the transmission one day and the replacment was only an M22 and the wrong ratio for the car. I hated driving it after that. I actually traded it for a 300zx turbo that had issues, but thats not the sad part. The guy I traded it to didnt put the title in his name immediately and less than a month later it was stolen...with the title in the glove box :3d_frown:. It reappeared a couple years later, found by a friend on a chance driveby. I spoke with the new owner, a soldier from Davis-Monthan AFB who had gotten it from a police auction with a blown motor, stripped interior and someone had started to try to remove the flares. I hope they guy was able to bring her back to glory.