If the head is cracked on the engine, do I just order new heads? Is there any concern with them being newer than the block? Keep in mind I am not an engine guy.

The port transmission leaks transmission fluid into the V drive. I believe that it just needs its gaskets replaced. The starboard has a "dirty neutral". The prop shaft spins when in neutral. This might be a release sping or forward clutch plate. It also tends to burn up its tranny fluid. Don't give me credit on the transmission troubleshooting, those conclusions were in the manual.