I've owned so many trucks and old cars, that I have to spend some serious thought processing to remember them all. But I can tell you this, from my experiences, the old stuff has soul. My driver is the 64' that belonged to my grandparents, and it's the truck I got my DL in when I was 15. I drive it every where, (just finished a 2500+ miles trip) and pulled a car trailer all the way home from Kansas, and every time I stopped for fuel, someone wanted to ask about it. It gave me a few moments where I was wondering what I was doing attempting this adventure, but with the right frame of mind, that's what it was all about. An adventure. We made it home, I've got lots of new memories, met lots of good people, and now I can start working on the 38' that I've been trying to get home for over 3 years.
You can ask 20 people the same question, and get 20 different answers about which truck is the best. The only thing to remember is that it's going to be your ride, done your way, so pick the one that trips your trigger. In time, with a little luck, you'll be able to own several. Good luck, and know that the folks on this site are some of the best people you'll ever meet and they all share a passion to keep the old stuff alive and going.
Id rather drive my old truck than have a new one in the drive.
Tramp