A lot of work!
If you consider the negative impact on resale value, its going to be cheaper to give away the 440 and buy a Chevy motor to put in the truck.
A Chevy small block was available in your truck, so putting one in can be done with stock parts, and it looks like it belongs.
The resale market will accept a Chevy V-8 in almost anything, and will pay a premium for a hemi if done right. But an old wedge isn't a real popular motor these days, and will reduce the value of of most any non-Chrysler you'd put it in.
