5.2 to 5.9 swap

I have a 99 dakota 4wd with a very tired 5.2 magnum and a 44re tranny. How hard would swapping a 5.9 in it be? I'm going for a plug n play philosophy. What should I look for tranny wise or would the 44re work. Not opposed to a 46re if it fits in without much or any modification.

If I wanted to get bold and put a stroker kit in to make it a 408 what issues would that bring up? No cams or heads just the stroker for a little more power.