440 cid, combo suggestions?

IMO, indys are a waste of money to get to the HP level he desires.

Ported E-brocks or 440source heads cut to about 72-75cc's will get him there with the right camshaft and other components. Getting to the higher HP number range is going to require a bump in compression. If you are planning on making some bigger HP later, buy a set of Victors and T&D rockers.

Rockers, get a set of ductile irons if you can find them. Run a good solid cam or small roller, RPM or Victor intake, 950hp and good headers and you should be in the ballpark.