I love the older trucks, as most here do. My 01 is so comfortable, the interior is in beautiful shape, and even though it’s rusty, I don’t care, I could care less how people perceive me based on my vehicle.
With that being said, I have a new truck. There is something nice about the reliability and warranty when you are out on the road. I tow heavy and often, so I have a Diesel. I don’t like leather, so I have an LT. It’s been a great truck. But if I was just running around close to home and just occasionally towing not much weight, there’s really no reason to have the truck and especially the Diesel. And the STUPID HUGE size really really sucks, I hate it, there’s no reason for them to be so big and so tall.
Continuing that thought, and I think it was brought up already, would you consider a gasser? They have the Allison 10 speed, they make great power, reliable, much less complicated, less emissions, and just a nice drivetrain. Unless you are racking up tons of miles with a lot of weight behind you on a regular basis, the gasser is more than enough.
As far as price, people regularly say these trucks cost $80,000, or $100,000. And that’s true if you throw a bunch of money at options that likely will never get used. You can get a very nice gas truck in the low to mid $50ks, and even a diesel if you really felt you needed it for $60k. Still a lot of money, but you don’t need to spend $80k on a truck that has a few extra cameras and a fancy badge on the side. A WT or LT will be magnitudes “better” than your LLY as far as options and stuff.