Welcome aboard!
Hopefully you will get some specific answers, there are plenty of these "swaps" around.
I thought that the biggest headaches with the swap was when changing to the "6-bolt" block, which requires bellhousing and clutch slave cyl changes (like on my car). Pretty sure that Tom Calvert has this [5-bolt hi-po 289] set-up, maybe the Jeffers’ also. The Tiger Auto gang in Dayton has surely been down this road, too.
A suggestion – since this forum is not exactly "hopping" with activity… an email or phone call to the right guy might get better response.