It sounds like an interesting project you and your Dad are working on. I am working on a similar project, a 57 that my Dad gave me a lot time ago. I hope you find the following helpful.
I’m going the same route as you a 440, go big or go home. Now if I had to do it all over again I would consider a stroked 360/340 with a turbo.
To free up some room on the driver’s side, I made the centre line of the drive train ¾” off centre towards the passenger side. This helps with the headers and the steering, but I still had to do some mods to the frame…..cutting and re-enforcing. I’ve install a mustang II with coil overs, however moving the motor over might give you enough room to slide the steering rod pass the manifolds. It will also free up some room on the firewall if you put a brake booster on it. Attached are some pictures of the steering linkage.
Goodluck!