Originally Posted by Jellby
Welcome to the amazing world of "Why regular expresions tend to fail when converting straight quotes to curly quotes"
May I suggest you use different markup for right single quote and apostrophe (both displayed as ’ )? That way, it would be fairly easy to change from US- to UK-style or vice-versa afterwards. In my files I use "’" for right single quotes and "& #8217;" (no space) for apostrophes, they encode the exact same character, however.
This is an excellent idea. I had this thought of making the apostrophe unique, but I didn't have a specific plan, and I didn't know if it was considered good practice. It makes perfect sense for conversion.