Well, once again after days of searching for answers and finally posting a question about it I figured it out on my own.
In case some other poor soul runs into this problem, this is what fixed it for me:
First off, my dialogue was all under a unique quest. I didn't use the vanilla "DialogueFollower" quest. I made a copy of it and copied over individual dialogue choices I wanted to use.
In my naivety I assumed all info would copy over exactly like it was in the original quest so I could simply make my changes and it would be done. What I failed to realize is that the scripts that copied over tried to adjust automatically to the new quest, which almost worked. Unfortunately there are just a couple of things that it didn't get right on it's own.
That would be under "DialogueFollowerScript" under the "Scripts" tab in your quest screen. If you double click on that and bring up the properties for the script you can scroll down to "pFollowerAlias" (and / or "pAnimalAlias" if your follower is an animal).
There you'll see a property with your quest name and below that a blank property (Uh oh!). I was unable to leave my quest name in the first box. I had to change it to "Dialogue Follower" and the second box to "Follower". Obviously for pAnimalAlias you would want it to be "Animal".
This magically solved my issue completely. There may be other problems with some of the other properties, but they haven't surfaced for me yet. Everything seems to be working perfectly.