Greetings everyone!

Just wanted to post some information I have found, since surely there are other trackball users out there and I have not seen any mention of this issue yet. Essentially, any Kensington device that uses Trackball Works (v1.0.4) has extreme click-detection issues when playing Skyrim. I have consistently duplicated this issue across multiple computers with multiple Kensington devices that must use Trackball Works (Orbit, Slimblade, and Expert Mouse). Even with disabling every feature through Trackball Works, Skyrim will still sporadically fail to detect clicks as long as Trackball Works is running. Closing the program will immediately stop this from happening, but it leaves one with a mostly unusable trackball (especially if you are using a Slimblade).

TL;DR
Kensington Trackball Works causes Skryim to fail at detecting mouse clicks. If you are experiencing this, try and use some of the mouse corrections on these boards to see if it works, if not, kill Trackball Works before playing and max out your sensitivity as a temporary fix.