Ive got a 2000 dakota quad cab, wondering how difficult it would be and if its worth it to put a 440 and 727 trans in and what kind of power i would get on a stock rebuild. Also any input is good input thank you!

 

A few people have done 440 installs. Check the FAQ in this section.
As far as power on a rebuild, you will most likely get manufacture HP ratings, remember those are at the engine, you loose a lot by the time it hits the tires/street. Check the FAQ for HP ratings.