Rounding Error for Screen/Printer Fonts

I am trying to attain a WYSIWYG for desktop publishing
software that I am writing. I want the on-screen appearance
to exactly match what the hardcopy printout will look like.

Is there ever a case when the rounding error between the
screen resolution for a font, and its printer resolution results
in the requirement to place the screen characters closer
together so that they will more closely correspond to the
precise positioning of their printer resolution placement?

Example: I have noticed that Times New Roman 12 Point
bold must have a little extra space placed between its characters
so a screen capture printout will correctly overlay a regular
(non screen capture) printout, as seen on a light table.

Is their ever a case when this little extra space is a negative
value? In other words where the characters must be placed
closer together rather than farther apart? If the answer is
yes, then please cite this font's name.