Opinions on 360 vs 440

It has already been mentioned, but what are your goals? What do you want?
This is just my opinion:
You can easily get 400 streetable HP out of a 360. 400 HP in an A Body is a lot of fun. To get 400 HP, you will likely have a choppy idle, but I love the sound of my modified 340.
If you want a LOT of HP, then go with the 440. If you are looking for the "Ooh Ah, it has a 440" comments at a cruise night or car show, then go with the 440. If you want the bragging rights of owning a big block A Body, then go with the 440. The heart wants what the heart wants. IF, DEEP DOWN INSIDE, YOU JUST WANT THE 440, THEN GO FOR IT.
However, if you just want a good cruiser that can still scald the tires, then go with the 360.