Considering a '67 Dart GT Convertible as my first project. Am I insane?

Wow that's quite a story. Thanks for sharing. It is so weird too, because I've been looking at an ad for a '67 Cuda Fastback 383 4 speed for like the last 30 minutes. Blue with a white racing stripe and a white interior. It is a beauty. They are asking way too much for it ($25,500 as a driver, not a show car), but I think I am going to go see if they are willing to deal.
The early big block factory builds do cost more. My seller was original owner, knew what he had, guaranteed me I could drive it across country. New hoses and fluids, 5 new tires, ready to go. He was as pleased to see it go to a good home as I was with the purchase. No haggle.
Get this... my neighbor and long time friend, he is 65 yrs old. He's been wanting another 68 Camaro since he gave up his about 40 yrs ago. He has the 50K to put into one too. So for months he has looked at them on the web. When he did drive about 300 miles to look at the one he wanted, he found he can't get in and out of the damn thing today. He is quite tall and his knees are weak.
Now he talks about pulling the 302 from his Silverado for a crate 350, repaint, etc...
My point in all this... try to figure out what will be right for you today and tomorrow. Good luck