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Get a cheap old 2-bolt, cast-everything small block chevy and rebuild it (then sell it), so that you get a feel for things before you start building a hefty, 4-bolt, forged-everything performance motor. I did that way back in the old days with a Ford 302W and it taught me a lot.
I just rebuilt mine for the first time and am planning on starting for the first time tonite. You will find that the machine shop will take care of some of the particulars . I bought a book called :How to rebuild the Small Block Chevrolet. It had pictures and detailed the process. I certainly learned a lot from this experience even though time will tell if I got it right. A crate engine is going to be cheaper and faster once you add up all the little and big expenses however I wanted the learning experience personally. I found that there is nothing that is really hard about the process- meaning I didn't get too stumped on any part of the process for very long. Take your time- do things right- you will have a million questions- which is Ok.