Congratulations. I like your idea of getting an older truck. In addition to being much more unique, it's also easier to work on. I'm willing to bet that the price you will have ended up paying for the '66, will be less than you would have paid for any modern headache, I mean truck, even after the minor repairs that you have noted. There's a landscaper in this town that uses a 58 Chevy, and it always seemed to me to be a great idea for free advertising. You notice his truck-in a positive way-much more than any F150, Silverado, etc. that the other landscapers use. Lucky for us that not many people take such a sensible approach, otherwise our hobbies (trucks) wouldn't be nearly as affordable.
Oh, and it's great to hear that your daughter wants to learn to drive the old three on the tree. I really appreciate a girl (or guy) who can drive a stick. One of my room mates and I used to joke about it in college, but I ended up married to a woman who drives a stick, has never even owned an auto, and doesn't plan to ever own an auto, if at all possible.