Thank You all for the good info. Like mentioned earlier, I dont know much about diesel engines so this is going to be a good learning experience. That's some heavy towing alright!!!
I am going to keep pulling the trailer , in the mean time it sounds like I have some money to save up for parts. Its going to be a good project to have done by spring.
If anything I'd upgrade the stock fuel pump asap and get a fuel psi gauge that'd be my main concern and keep the rest stock till you can address the trans