Ubuntu – Wine cannot find the FreeType font library

Ubuntu 16.04 LTS 64-bit
All packages currently up to date as far as I can without going to 16.10 (I can't do a distro update as I am a first responder and my radio gear will not work on 16.10 as of yet).
Laptop is currently configured the same, yet it seems to work just fine, so I'm not sure what's causing this.

When trying to open simply Notepad, I am given the following error:

brandon@BrandonsDesktop:~$ wine notepad
Wine cannot find the FreeType font library.  To enable Wine to
use TrueType fonts please install a version of FreeType greater than
or equal to 2.0.5.
http://www.freetype.org

The window opens, but the menu bar is blank and no letters type out, in fact doing that brings up an invisible Program Error box that has to be closed by the task bar.

What I have done to attempt to remedy this:
Purged Wine, libfreetype6, ttf-mscorefonts
Then did the following:

rm -rf $HOME/.wine
rm -f $HOME/.config/menus/applications-merged/wine*
rm -rf $HOME/.local/share/applications/wine
rm -f $HOME/.local/share/desktop-directories/wine*
rm -f $HOME/.local/share/icons/????_*.xpm

I then reinstalled WINE, but the same issue ocurrs. I'm not even sure why it's doing this? The only configuration difference between this computer and the laptop, is that this computer has 3 monitors.

Any help is greatly appreciated. Thanks.

I made a video demonstrating the issues it's showing me, 10 minutes long, but maybe you'll catch something in the terminal that I missed?

https://www.youtube.com/watch?v=SXGe-lo4haw

EDIT: I have tried the latest winehq packages, wine-staging, same issue as before.