I have only bought new twice. A 82 Chevy C10. I sold it when they were starting emissions testing. I wasn't about to put all that crap back on. It had over 300k but was still going strong. And a 2000 Expedition. I still have it. Its only just over 200k. I have a 56 Chevy 3/4 ton, a 98 Z71, and the use of my son's 07 2500HD Duramax that may be mine soon. I don't see the need of ever buying another truck.
I am a tinker, so it is pretty natural for me to buy broken things and fix them...
But part of it is requirement - Straight axle, stick, and bulletproof drive train... By the time I had the money to buy new (90's), there wasn't nothing left to buy.
I keep trying, but I can't get out of the 80's, except for my 98 caravan.
I have one more truck on the docket...
Looking now to put together a 1T heavy dually dump bed.. Straight axle, 4" lift, with a nice flat-top 350, a Muncie 465 with a Rockwell drop-gear overdrive and a NP205 transfer. Dana60 front, Dana80 in back... 4:10s/4:55s... Something like that...
Probably 70's/80's, but it might be fun to take a late 90's 4dr, put a decent frame under it, turn it analog, and shove it all on there. Then I could have butt-warmers... and cup-holders, and haul some of my grandkids up fishing.
I will make one more, one more time, and won't need another.
Then I will take the one I have now, give it a porker, sky jack it, and use it to play.