There are 2 large Area Places with the same name, which also can't help with navigation, these should either be uniquely named, or combined into 1 Area mapping.
 
There is also no point having a PLR segment as the only extension of a Private segment. You are adding a needless routing penalty, this should be combined as one or the other.
 

To be honest WME has been so unpredictable lately you can make almost any change, save it and find it has worked fully, partially, or not at all. Regardless of the confirmation message or what the screen shows after the save.

Done
 

Guess I forgot to hit save before I went to bed, as I remember combining the two areas while I was adding the road.

Thanks for pointing it out