Interesting! I never noticed that this won’t extend over automatic “variable” text. I’m not sure how you would set this up automatically (and still use the Text length)

How are you planning on producing the final work? Will it be Publish Online? Fixed Layout EPUB? You can probably use the same export format for them to view a proof.

Wow, using an Illustrator EPS is a sad solution. Ouch.

This script would have helped: https://creativepro.com/easy-diacritics-and-other-tough-glyphs.php

Once you have one of them, you could probably copy it and then use find/change to replace the others… see tip #5 here: https://creativepro.com/10-findchange-tips.php

It’s very easy if you have a sharp pencil or a good pen.
Just kidding! :-)
This might help: https://creativepro.com/finding-and-changing-glyphs.php
(That assumes that there is such a character in your font… an omega with a dot over it)

Some people have also reported this problem with the squares in the right column of the Layers panel. Did you recently upgrade to 2015.4? Are you on Mac or Windows? Have you tried rebuilding your preferences yet?
https://creativepro.com/resources/faq

Taking a Lynda.com course is a great idea, Dan. There are a lot to choose from, including my Essential Training course and others.

We have some templates here on this site (see the two template pages in the Resources dropdown menu in the black nav bar at the top of the page), which might help. But there’s nothing like knowing your feet are under you when you start a project.