I think you might enjoy a little book called 'Words fail me' by Teresa Monachino which is about word oddities.
Here's an example:
"Finally the bill would go to the House of
Lords where we would hope that those tit-
led gentlemen may defeat it."
This is from the section which explores words which change their meaning with the addition of a hyphen, yet both forms could technically be appropriate.
She also asks such questions as "Why does monosyllabic have five syllables?"