Error File - Rely on System Fonts

When creating PDFs from Word and Outlook, I frequently get the error message shown at the bottom of this post.  The error message comes in the form of a text file (instead of the PDF) that's created when I try to convert.   

I learned a while back that this can be avoided by going to Windows Printing Preferences and unchecking the box that says "Rely on system fonts only: do not use document fonts."  However, the software periodically changes it back to having that box checked (resulting in error messages again).  Today, the software wouldn't stop generating error messages on the document I tried to convert until I closed out Word.  My questions are:

1) Why would anyone want this box checked?  

2) If Aptos is not a common font, why would this not be included in System Fonts?

3) Why does my preference get changed back periodically?  Is there a way to make this stick?

4) Why would a company as sophisiticated as Adobe default to something this dumb and annoying?  I like my prodcutivity software to make me more productive.

Someone please help me make this stop!

%%[ ProductName: Distiller ]%%
Aptos-Narrow-Bold not found, using Courier.
%%[ Error: invalidfont; OffendingCommand: xshow ]%%

Stack:
[77 77 77 0]
(

)

%%[ Flushing: rest of job (to end-of-file) will be ignored ]%%
%%[ Warning: PostScript error. No PDF file produced. ] %%