After using this setup for a while, I have more info. It works pretty well, the trans usually runs at about 150 on a hot day and rarely goes above 160 with the fan on unless I am pushing it. I would say this setup works about as well as the cooler I had in front of the condenser when cruising down the highway and it definitely works better than my previous cooler when sitting in traffic since it has its own fan. I don't see the trans temp becoming a problem with this setup as long as the fan is on. I'm guessing installing the filter will reduce temps a couple more degrees since it will add surface area.
The one problem I am having is that crappy eBay fan is starting to squeal and grind, so I am not expecting it to last too much longer. I am planning on getting a Spal fan to replace it with, but I need to measure to see how big of a fan I can fit on that shroud since I would like to get their 9 inch fan if possible. I don't like the looks of their 7.5 inch fan because the motor is ridiculously big compared to the blades, creating a significant dead zone in the middle. Either way I'm sure it would work better than the crappy fan I have on it now though, that thing is a noisy piece of crap.