Chris,
I'm re-wiring my '59 right now. Ran out of time sunday so will be installing the rest this weekend.
I bought the chevy duty harness for $100 and got a new dimmer switch (moisture prone, being on the floor), headlight switch (was completely wornout), and bulbs.
I spent about 2hrs removing the old wiring, headlights, taillights, grill, instrument panel, etc. I was able to wire the starter/coil harness, headlights, and taillight harneses in another 2 hours. This weekend I'll install the two (main) harnesses that run the light switch, instrument panel, and key/ignition and I'll be ready to ops test it all.
This kit is SO simple. They number each end of all the wires/connectors and list the name and disription of what and where (exactly) you install each. (Example: #29 to top terminal of ignition resistor) You get the point!
This kit will supply the wiring from headlight to taillight minus the "radio, a/c, or anything else non-stock"
I'd say rewire the neccesities and then find your power to tap into for your radio after you install this kit, tidy up the wiring, and become much more familiar with you truck and how its wired. Its intimidating at first but once you look at and understand what your pulling out and installing you'll really start to get comfortable with everything.
Edit: They offer a genrator or an alternator harness. So with your sbc running an alternator thats the only differance you'll need to worry about. Dont mount everything back into its normal position (lightswitches, instrument panels, etc) to check for high current/ hot connections/ smoke, the unlikely bad stuff.
Good luck, keep a fire estingusher in your truck.
Jason