So, running those three lines though your script I got exactly what you expected: 
Course\x{fffd} Syllabus\x{fffd}
Operator\x{2019}s Manual 
Windows\x{00ae} Version 5.2

[download]
Now, I can think of several ways to go from here. My converting to hex (in my update above) worked but wasn't really ideal (the (R) mark would have been tossed).

If your goal was to convert those three lines into this: 

Course Syllabus
Operator's Manual 
Windows® Version 5.2

[download]
What would you do next?

Thanks for the help!

In reply to Re^2: Matching  & € type characters with a regex by Rodster001
in thread Matching  & € type characters with a regex by Rodster001

Title:
Use:  <p> text here (a paragraph) </p>
and:  <code> code here </code>
to format your post, it's "PerlMonks-approved HTML":


  • Posts are HTML formatted. Put <p> </p> tags around your paragraphs. Put <code> </code> tags around your code and data!
  • Titles consisting of a single word are discouraged, and in most cases are disallowed outright.
  • Read Where should I post X? if you're not absolutely sure you're posting in the right place.
  • Please read these before you post! —
  • Posts may use any of the Perl Monks Approved HTML tags:
    a, abbr, b, big, blockquote, br, caption, center, col, colgroup, dd, del, details, div, dl, dt, em, font, h1, h2, h3, h4, h5, h6, hr, i, ins, li, ol, p, pre, readmore, small, span, spoiler, strike, strong, sub, summary, sup, table, tbody, td, tfoot, th, thead, tr, tt, u, ul, wbr
  • You may need to use entities for some characters, as follows. (Exception: Within code tags, you can put the characters literally.)
            For:     Use:
    & &amp;
    < &lt;
    > &gt;
    [ &#91;
    ] &#93;
  • Link using PerlMonks shortcuts! What shortcuts can I use for linking?
  • See Writeup Formatting Tips and other pages linked from there for more info.