I am working on an MS Word document that contains many, many Heading 5's.

If I happen to change one of those headings so that it contains
the word 'Good' in bright green, I want that same color to appear
in the Table of Contents.

In another Heading 5, I might have the word 'Bad' in red.  Again,
I want this red 'Bad' to appear in the Table of Contents.

(1) Is there any way to make this happen?

(2) If not, how do I change the Table of Contents to a uniform font (such as
    Courier New)?

I don't think (1) is possible unless you update the TOC entry
yourself, which it sounds like you want to avoid (if you do want to do
it this way, add the \MERGEFORMAT switch to the TOC field code so that
the formatting will be preserved when you update the field).

(2) is easy enough, though. Go to Format > Style... and edit the TOC
styles (as many as you have levels in your table of contents, so at
least TOC 1 to TOC 5). Select each style and click on Modify, then on
the Format drop-down in the dialog box that appears. Select Font and
you can change the font details. You can also change the layout
settings and various other settings here.