Well I did the install that night and everything went fine...
I didn't mess with any of the fittings going into the radiator in fear of breaking them; instead I just used a tubing cutter and split the return line right in the middle and then plumbed it in there. It made the tube routing pretty easy.
Three days later, no leaks and there is a huge difference in the send and return tranny lines. The cooler seems to be working!