Thanks for all the feedback everyone. A lot of good points brought up and a lot to consider. At this point, we're going to see if we can get out of the SBC/TH400 what we want. If we can't, we will probably keep it and make some upgrades such as Edelbrock PF4 or Holley Sniper EFI and maybe an overdrive trans.
I won't be disappointed if we stick with the 383. It is well built and with an overdrive trans and EFI it should run quite well. If we go that route, we will probably aim to keep the truck more original. I've seen a lot of nice-looking 67-72's in black that look fairly original. I watched Dazed & Confused years before I bought my 68 and the black Cheyenne in that movie really caught my eye. That and project Copperhead of course.
I have an itch to do a Gen V LT swap into something and there are other opportunities for that. I've been keeping my eye out for an OBS (88-98) pickup because my dad wants one so that might be the better opportunity for it. Especially if we end up with the one we're looking at tonight which has a V6 with a manual trans.