I know it may help extend tranny life, but if your tranny is worn a bit, will having the cooling kit be worth it? How does cooling help shifting and performance?
It has no effect on shifting and performance. Then why bother? Well, it you do a lot of trailer pulling, or climb a lot of hills, it's well worth it. The transmission, like everything else, has a temperature range it works best at, and if you get it too hot the fluid can actually boil. The transmission cooler runs the fluid through a small radiator and keeps it in it's desired operating temperature range.
I'm no mechanic, but I can tell you that my ex boyfriend put one of these in a truck we had a few years ago and it made a WORLD of difference. We, as the poster above me stated, did pull a trailer quite often and we also climbed a lot of hills.
If your transmission fluid isn't burning up or boiling off, then a transmission cooler isn't going to make any difference. Those add-ons are intended for vehicles that pull trailers or other heavy loads. It's very simple to tell - if your tranny fluid tends to darken quickly and you keep having to add more, then that means it's overheating and being stressed out. Otherwise, if you want to maximize the life of your transmission, just change the fluid regularly (preferably using synthetic ATF, pretty expensive but it lasts longer) and dont abuse your transmission (i.e. don't shift it into drive while your car is still backing up, don't play with the accelerator causing it to downshift more than necessary, etc.)