Much like Ken's post....I admit to not bein a Caddy expert, and my advice should be taken as such.
Bein a motor guy, and the things I've seen of the Caddy....The bottom-end looks to be solid, and capable of some decent HP/TQ (Well beyond it's original design). The heads look fairly decent for their era, and with the right masaging capable of some good numbers as well. But just like any other luxury car engine, it's designed for smoothness and bottom-end TQ, and the oiling, as well as cooling systems are maximized for low RPM. The minute you put them in higher RPM duty, the system has to be re-thought.
If you run DD, the engine should be pretty spot on for the avg guy, but will see more load than it was intended being in an airboat, and will create more heat/stress.
If you put a gearbox on it, and spin the RPM up....Put some race engine thought into the oiling, using some simple fixes, and do the same with the cooling, and I think the engine would make a serious player. I.E. All the engine "should" need is consideration to the increased velocity/volume of the oiling and cooling system, and I see a killer engine on the cheap. JMO
I'll be happy to share some 411 on what I mean about cooling system pressure drop/flow manipulation, and oiling system design parameters with consideration to flow/cooling/shear, if you find you're in need. But be warned...I don't know Cadillacs...Just metal parts that perform a function.