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If you could find a marine head gasket for a 300, that might be a little better. I'm not sure if they're just thicker or stronger or both, but most high performance Cummins running insanely high boost put in marine gaskets and head studs instead of bolts. I'd venture to say that you could get a marine gasket and then bore the holes out for a larger head stud, then put studs in it. You might be okay then as far as the head goes.
Another thing, the first gen Cummins with the VE rotary pump had angled piston faces as well as angled injector ports. The injector does not sit directly on top of the combustion chamber so these maaaay... work in your 300 spark plug holes. That's a BIG maybe though. Any way about it, it's going to take a lot of work.
I would go with a longer stroke, just to take advantage of having the diesel to begin with. I would also go with a direct injection system, NOT an IDI system as was hinted at earlier. Those IDI diesels aren't worth a crap.
If I were you, I would just buy a 4bt or 6bt for cheaper than you're going to fix these 300's, but that's probably out of the picture. If nothing else, I would go buy an old 6bt just as a model so that you would have at least an idea of what your 300 should look like and run like when you're done. Just my two cents.
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