1984 S10 Blazer 2-door 2wd 2.8/5-speed. Bought in fall of 91. Totalled in the spring of 2000.
1989 C1500 Cheyenne regular cab/long bed 305/700R4. Bought in spring of 2000. Traded in spring of 2005.
2005 GMC Sierra SLE regular cab short bed 2wd 4.3/auto. My first new vehicle. The truck I could afford new. Traded spring of 2008.
2008 GMC Sierra SLE regular cab short bed 2wd 5.3/auto. Still have. My daily driver.
1982 Pontiac Grand Prix Brougham. Bought in fall of 2014. Hasn't run since December 2014. Still have. Work in progress.
1996
Buick Roadmaster Limited Collector's Edition sedan. LT1/4L60E. Bought in the last days of 2019. Still have.
I guess I hang onto my stuff. 4 daily drivers in 30 years.
I forgot one. Surprising, since I haven't owned that many compared to most of you.
2002 Ford F250 Lariat Extended Cab/Long Bed 2wd V10/Auto. Bought in 2012 from my best friend, who bought it new. I bought it to daily drive while I did the cam/torque converter swap on my 08 Sierra. It was really down on its luck when I bought it. My friend had a bad drinking problem and had really run it into the ground. I paid too much for it to help him and then put a ton of work into it. I basically broke even when I sold it so all my labor bought was having something to drive. It also gave that truck a second chance. When I bought it the tires were shot, the front brakes were shot and three of the wheels were damaged from hitting curbs. Almost nothing worked. I fixed the power windows, mirrors, locks, the cruise control, the overhead console trip computer, the keyless entry and got the rear doors where they would open and close (broken door latch cables). It was a smooth driver when I sold it. It needed a lot more and I wanted to give it more, but I couldn't keep it. Gas prices were high back then at it was a real hog. It got 11 MPG all day, no matter how you drove it, with or without a/c. It had like a 31 gallon tank and $100 wouldn't fill it up. I sold it in the fall of 2012. I miss that old truck. It really grew on me. It had that sure feeling that only a heavy vehicle has. It had new Cooper all season tires on it and it felt just as sure of itself in the rain as it did on dry roads. I don't know what the specs on the V10 were but it had a lot of torque (at least empty) so it felt pretty good. I never hauled anything in it or towed with it. If I could have kept it, I would have. I didn't need it though and it was in the way at the house.
I regret the S10 Blazer getting totaled but the wreck wasn't my fault. I was building a 305 to swap into it when it got crunched. I still want another square body, two-door, 2wd S10-Blazer. I would swap in a 5.3 instead of a SBC at this point though.
I regret trading in the 89 Chevy. It could have been a really sweet ride if I could have kept it but I didn't have the money at the time to do what I wanted to do and it had become somewhat unreliable. I was using all my spare time and money keeping it going and I burned out on that.
My only regret on the 2005 Sierra is buying it at all. It was a nicely equipped truck (power windows, locks, mirrors, tilt, cruise, intermittent wipers, etc. but I didn't want the 4.3 and it was a dog. Still, it was a bridge to the truck I have so not a bad deal in the end, I guess.