A couple of guys on here are real diplomats. They have nicely stated that getting too crazy with your plans will end up in another eBay basket case. I'll be more blunt. Have you actually even driven the truck? The 1960 front end is a high tech front end from GM which rides nicely if properly maintained. The steering on a 1960 shortbox Chevy is some of the lightest and easiest you will ever find. Don't listen to your friends, whom i'm sure have "done it all", nor the magazines which want to sell you parts. I say keep the front end, fix it properly, do the brakes, get the engine running and drive it. That's the absolute cheapest start you can have. THEN, when you want to "improve" then you can swap in the 327. And a different transmission. (you do know that you can have overdrive without having an automatic, right? Think T-5 or a Borg Warner OD on an original 3 on the tree)
My advice is to SLOWWWWWWWWWW down, get a handle on actually getting the truck into a driveable, safe condition and then make modifications as necessary, and as funds allow.
