I couldn't figure out how to "read" all the characters in the sentence in the format of "words.special_character", but I realized that if I replaced all period+special_character instances in the Word document, all my For Each loops work. I used the following code at the very beginning of my sub module and everything worked as expected:
'Adds a <SPACE> between a period and a non-alphanumeric character
With ActiveDocument.Range.Find
.Text = ".([!0-9A-z ])"
.Replacement.Text = ". \1"
.MatchWildcards = True
.Execute Replace:=wdReplaceAll
End With