For me, buying new makes more sense then buying used these days. Used to be if you looked around long enough you could find a nice used truck for thousands less then a new one. That's rarely the case anymore. Now the one's that have 2 or 3 years of average miles on them aren't that far off in price of a brand new one. I'm talking about used trucks, as I've never owned a car, suv, etc. Maybe you can still get a deal on a used one of those but truck values have skyrocketed the past few years. Huge demand for them. Why should I take a huge risk in buying your truck with 50,000 miles for $4-5,000 less when I can go buy me a brand new one, have a full warranty, free maintenance for a couple years, better financing, etc? Not to mention if the new one turns out to be a piece of crap there are lemon laws that protect me, not the case when I buy your used truck that you swear "is in great shape and never been off road or abused!". Not only that but the car dealers around here are famous for putting the biggest piles on used junk on the lot you've ever seen and slapping a premium price on them. Either that or the lots are full of retired rental vehicles. I remember trading in my 2011 GMC SLT with the 6.2, it was clean with only 15,000 miles on it. It never sat a day on the lot I traded it in at, nope it got hauled off to some auction and who knows where it ended up. You just can't find good local trade-ins around here anymore. They're all imported from places up north or who knows where (I run the VIN's to check out the history).
I'll keep a truck as long as it's running fine with regular maintenance. I had to get rid of two trucks that were running fine but I'd hit 3 deer with one and didn't want to claim it on my insurance again and the a cop at a license check told me to get my front grill and headlights fixed of be ticketed. I would have had to pay thousands out of pocket on a truck that had 128,000 miles and was 7 years old. Another truck was a 2000 Silverado with 250,000 on it that a deer totaled and the insurance company gave me $1,000 MORE then what KBB said it was worth.
I don't trade just to trade usually. Recently got rid of my Tacoma because I made a mistake and had gone with too small of a truck. I'd owned 1/2 tons before but thought I could get by with less truck. Lesson learned. I don't need to have the latest and greatest, but I am not one that will keep a truck just because. If I need more truck then I need more truck, or I don't need to be shelling out thousands on a 7 year old truck just to get it repaired to avoid being ticketed.