So I discovered why the plugin only works on the first run of After Effects. I originally installed the plugins right after I upgraded AE thru Creative Cloud. When I started up AE, it imported settings from the previous version and ran as expected. I verified the plugin worked and it did. A few days later when I went running AE, it would crash. It turns out that if you delete the AE preferences in your %USERPROFILE%\AppData\Roaming folder, it will again startup and work until you restart AE. So the issue seems to lie in that somewhere.