Wow, thanks a bunch guys. I didn't expect that much of a response so soon hahaha. To try and add a little context and answer some questions I'll add the following:
The reason that I want to stay away from rebuilding an engine myself is that I don't have the knowledge to do it myself. I consider myself pretty could with my hands and a reasonably intelligent person but as part of that I understand my limitations. This would be one of those

I'm not sure what I'd like for an engine yet and am open to some more thoughts on that front as well. I'm definitely looking for more than the stock engine would give me but at the same time I do plan on driving it on the streets so I don't need to go too crazy. That fast burn 383 sounds like a strong candidate.
It sounds like my best option here is a crate. From the sounds of it I "may" be able to get a better deal on a rebuild but unless I happen to find someone doing it on the cheap it'll be comparable to a crate.
My pipe dream is to keep a three speed column shift on the truck just for looks and something a little unique. I'm not sure that I'd be able to find a three speed tranny to handle something like that.
Hollow65 where did you find that 383?
www.chevrolet.com? Once again thanks for your opinions.