Where to start on my 63 Dart?

It's an automatic. If those lines are the little ones that went into the bottom, I have to replace them anyways. Those radiators are pretty pricey though...

I found one for cheap in a junkyard.

http://www.slantsix.org/articles/supersix/ss-installed-sideview.jpg
I think the one that I'm talking about is the gray one beneath the blue one. With how little I know of cars, that's probably not a manifold. =/

Actually, that was my mistake - that is a manifold, and it's the exhaust manifold. I was thinking the "dandruff" was a type of corrosion you only see on aluminum.

Until I can get a hold of a camera, would you happen to have a picture of how the engine should look?

Yes, I've got a very good picture of an early Barracuda with the stock air cleaner and PCV system right here.

How hard would it be for someone with next to no car maintenance experience?

It's not much harder than changing a tire: You unbolt the wheel, pry the center cap off with a screwdriver, remove the cotter pin with a wire cutters, and then remove the big nut in the middle of the spindle. The drum should then come off if you pull on it hard. I'd probably have a machine shop press in a new bearing race. Not particularly hard.