'71 Duster 440 or 360? Pros and cons

I did the swap once before. In my thoughts... unless you are drag racing... the cost of rebuilding the 360 into whatever you think you will get out of the 440 will match whatever you spend to build the 440, buying a tranny, brackets (omfg don't forget having to find brackets), mounts, tranny mount, modifying the driveshaft.... etc...

As others have said, you'll get what you want out of the 360, faster and cheaper. Unless you are drag racing. With that being said, a 440 isn't a boat anchor and you wont' really notice the difference in handling either (unless you are road course racing).

If I could have done my motor swap different, I probably would have rebuilt my small block with more power than the big block ended up having, and kept the big block as it was a date code correct for my big block car in the garage.