PLA Filament Not Softening During Load w/ FlashForge Creator Pro
After all of this trial and error it was a simple solution.

I did not snip off the end of the filament after unloading. The filament had been tapered after unloading because of the way it was extruded previously. I don't know exactly why (please feel free to add to this answer) but when I made a clean cut on the end of the filament and then fed it through, it extruded with no problem.