Well, the swap is done!
Changed fly-wheels, manifolds and off we went!
The '98 tranny seems to be working just fine.
We may try to rebuild the HO at a later date if needed, it is locked up and I still have to take the head off to see the damage done.
As far as cost, he paid $1400 for the '98 and we hope to sell some stuff to get his final cost down to about $4000 for what he has to drive.
Thanks for all the input on the tranny, for a young kid it was a good experience!