As an update:
I re-installed Ubuntu and didn't bother installing wine anymore. Instead, I installed VirtualBox
and have XP running inside of the VM. I just have to setup the shared folder stuff now (I'll probably screw that up - but that's how you learn right?). Works well enough for now.
I didn't fully understand how to setup the VM that came with Ubuntu (at least to get the GUI up and running), and VMware was just too much (and I'm not paying for it).
. . . this is the digital projection of your mental self. . . .