Update: Strange...but whenever I do anything with the feature or content type, such as deactivating or activating the feature, it will route. But only once.
What I did this time was:
1. Disable-SPFeature and wait for it to complete
2. Enable-SPFeature and wait for it to complete
Then ran the appropriate timer jobs in the correct order and it routed. But if I add another document, it wont unless I re-run a command.