An aftermarket cooler is a great way to head off problems for any hard working auto tranny. Heat is the number 1 enemy of transmissions. The cooler will come with instructions. You have two options for hooking the plumbing up.
The easy way is to bypass the cooler in the radiator and run the tranny lines to the new cooler. The slightly more complicated way is to let the tranny fluid run through the radiator first to cool down some and then route it to the aftermarket cooler.
I use the second method. It gets fluid to the aftermarket cooler at a lower temperature and in turn the fluid returning to the tranny is that much cooler.
With the first method you just cut the two lines from the tranny and route them to the cooler.
With the second method you identify the return line from the radiator, cut it and route that to the cooler. To tell which is the return line you start with a cold engine and tranny, make sure you are not going to get grabbed up by any belts or fan blades and start the engine and put your hand on the two lines coming from the tranny. After just a few second of idle one will begin to warm up from the heat generated by the pumping process. The warm line is the feed line, the cool line is the return-cut the return and send it to the cooler.
One of the challenges with a CUCV tranny cooler is getting to the grill. You will likely need to remove or loosen the grill guard (what most folks call the brush guard)
Don't get too wrapped up in sizes or brand names. For me, I figure that bigger is better but, like you, I also live in a cold climate area and in winter I'm gentle with the tranny until we've gone far enough to warm it up.
Any parts store should have access to a wide selection of coolers
Lance