360 or 440 in my 68 Cuda?

I have a 360 in it right now with "J" heads and a few add ons. But I was thinking of....well......BIGGER :twisted:

Is it a real pain to drop in a 440?
If not bad then what can I expect to run in the 1/4 with a built 440 running maybe 150 shot of NOS?
I want 200 in a 2 stage but a buddy tells me i have a death wish if i do that.
Point me in the right direction guys :thumrigh: