It's understandable that my situation is hard to follow (I haven't come across any similar problems online).
When I attempt to install VMware tools from VMware Workstation 8 or 9 (tried both), I get that error mentioned above:
http://i.imgur.com/sPcIAZo.png
It's definitely related to the error I receive when installing VMware Workstation.
I get this error for each OS:
http://i.imgur.com/1f9qhB2.png
"linux.iso.sig" not valid short file name
"solaris.iso.sig" not valid short file name
"freebsd.iso.sig" not valid short file name
etc