Hi and welcome.....your parents named you "Jazzman"???? Your build up question can be answered very easily.....how much money do you have? Granted A Hemi/Torqueflite would look great but VERY expensive. Now if you have access to an original 331/354/392 that you can have rebuilt in a fairly stock mode with a little more cam then have at it.
Again it all depends on how much money you have to spend, the more engine you have, HP wise the more you will have to beef up the rest of the car. Don't know what you mean by a "common rearend" but I would just look for an 8 3/4 Mopar rear.
My budget would lead me to an old Motorhome with a 440/727 combo that you could probably pick up very cheap. Most of these are fairly low mileage. I would'nt go below a 383 for your heavy car, cost too much money to make enough HP to get it down the road. Good luck