Got it working... I'm not happy with what I had to do though.

I modified the path so it looped around three times as opposed to one solid loop. this allowed me to get one revolution out of the belt before it decided to fly off into space. Then I cut out that section of the motion path in the graph editor and repeated it post-infinity.

Less than happy having to do a complete work around like this to get something that should be so simple to execute working "correctly". If any of you come up with a better solution please let me know as I'm sure this won't be the last time I have to animate a belt looping around a flywheel.