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OP never said what generation 383 we are talking about either,that could help
...Or hurt. If he wants an LT1, he definitely needs to convert the mgt. system from a V8 car. If going old school, the conversion itself, as far as making it run, will be easier. Distributor/carb clearance would be one other issue.
Either way he still has the same issues with getting the engine in there. Other issues would be with emissions as I mentioned earlier, unless he doesn't get tested where he's at.
I had insurance agent ask me if we had swapped the v6 to the LSI when I went to get insurance! I immediately thought of the comments I have read in the threads about doing the swap and smiled!