Rotor - we did something similar with my '63. We used the tranny and engine from a '75 Chevy truck. We've always pulled both the engine and the transmision at the same time and re-set them together in the project truck. It is the easiest or fastest way? I don't really have the answer - it is the only way we've done it.
You've listed a lot of questions. You'll get the best response if you can break down your questions. Try to focus on your first challenge. What is it you want or need to do first? Then, let the guys know what you are getting stuck on. There is a ton of information here and lots of people eager to help.
I would also recommend you pick up Tom Brownell's "How to Restore Your Chevrolet Pickup" to get started. There is a terrific review of the book here if you'd like to read more before you buy it.
Also, try visiting the "links" section of the website to get acquainted with the vendors who supply parts for your truck. Woogeroo, a member of this board, has a nice list of links for his truck at:
http://woogeroo.home.mindspring.com/Matraca/matraca.html Good luck and enjoy your new project.