You could try to find a complete running vehicle for the swap. That way you would have the drivetrain, wiring, etc. I dont know what motor you are looking for but the 88-95 chevys can be found with throttle body fuel inj v8s, 5 speeds, and 241 cases which would be a little better than your 231 and still be a driver side drop. The 96-99/2000 body style chevys would be a better motor than the throttle body ones. The NV3550 5 speed is ok for a mild build, they were in the s-10 series and the light duty 1/2 tons and 3/4 tons. The nv4500 would be probably one of the best 5 speeds you could do if not the best. It can be found in the heavier 3/4 tons and the one tons.
Of course the LS style of motors would be better yet. Their cost is starting to come down also so they are comparable to the older motors. I know the 5 speed was offered behind the truck motors but not sure which ones. There was also a 6 speed, again Im not sure. Due to not selling as many of the standards they didnt produce that many per say. You can get adapters to do an NV4500 behind an LS style also. I dont think it was ever offered that way from the factory, but could be wrong.
If I were just wanting a v8 and maybe a mild build on it, I would find a 96-99/2000 body style chevy 4x4 one ton with the 350 and the nv4500 5 speed. Would give you the v8 power that you could build, would give you a stout 5 speed tranny, and a 241 case that will either be heavy duty or that could be made better. Think they offer kits to convert it to a 5 or 6 gear planetary gear from a 4 gear as well as a heavier/wider chain. Along with a slip yoke eliminator kit.
