Opinions on 360 vs 440

Build what keeps you motivated. I have a small block in an a body and love it. If I built a second I think I would be more motivated to have a forced induction /6 with a stick shift over a big block/auto but that is just ME. The small block will always be easier but based on your post it just really sounds like you want the big block and there is nothing wrong with that, it's been done a million times. Just remember to build the car that will keep you looking back at it in the parking lot as you walk into the grocery store.
Good luck!