Sounds like a perfect candidate for belt driven super charger, change the cam go have fun with it. Thick piston tops, low compression H.D. design pistons and valves that are made for abuse at WOT for long times pulling grades
I would try and get it running and then do a warm compression and leak down test on it and go from there, if it tests good go have some fun If not fix it first and then go have fun with it, I would shoot for under 8.0 lbs. boost on pump fuel with no inter cooler