I think my problem is actually a Bug.
For some reason the animation is playing all the way through but when it gets to the end my Main AnimBP is not being updated properly and so the State Machine on the other side thinks the Animation is still playing.
This causes the transition rule for Automatic and Time Remaining == 0 or even Time Remaining < 0.1 to fail even though the Animation is clearly over
To confirm this, I had it print to the log from my Linked anim layer True when the PlayTime was == to the Explicit Time. After the first time entering the state, the animations will hang at the end printing True to the Log, meaning that the animation is over but the MainAnimBP for some reason is not being notified.