Welcome to the 'Bolt!
A sbc is a lot shorter then the inline engines. A friend of mine has a 50-53ish 2 ton COE and hes running a 292 with downdraft carb. My father in law has a 1948 Dodge COE with a sbc also. It would be less work then you think. A sbc weighs about 150 pounds less then the old inlines and you can come up with almost any combination of carbs, intakes, fuel injection, to fit your needs or room.
I think your a little all over the place on where to go and what to do. First thing you need to do is decide what you want out of the truck.
Do you want it to go todays highway speeds? How much weight do think youll tow with it? How far will you travel? Theres a lot to think about when you consider how often or how its driven that you should really consider before making up your mind. Try to identify what it will be used for primarily and base your decisions off of that.
We'd love to see some pics!
Jeff