To be clear, this weirdness specifically refers to English spelling only. I don’t think the English language itself is particularly weird.
This is true, but again, this oft quoted characterization of English might give the impression that English is unique in this way, though other languages can have these qualities, too.
A hyphenated and a non-hyphenated word walk into a bar. The barman’s head explodes with irony.
And what’s all this with Colors? What are they trying to pull?
I’ve just noticed there’s also the negative word ‘con’ in ‘confidence’, as in ‘confidence trick’! So confidence must actually be bad… therefore I’m not so sure about the previous statement… er…
The OP appears primed for Rastafarian linguistics.
You have to take the death vibration out of words and replace it with a life vibration:
Instead of “deadline,” say “lifeline.”
Instead of “dedicate,” say “livicate.”
Instead of “appreciate,”* say “apprecilove.”
*Jamaican dialect often features h-dropping.
And why is “monosyllabic” polysyllabic?
Why do you park on a driveway and drive on a parkway?
Why aren’t palindromes palindromes?
Hang on, I think I did that wrong.
There’s also “pita” in “hospital,” so it can’t be all bad. (Of course, finding such substrings is nothing peculiar to English; I’m sure you can find examples in most languages. I’m having trouble taking the OP seriously here.)
Notice how “scam” incorporates “cam”, correctly implying that scammers are recording their victims on video. It all makes sense [del]when you[/del] if you don’t think about it.
Cognates are obviously named after the fact that the official arbiters of language had too much cognac at the time that they issued their decrees.
And don’t even get me started about driving on a parkway and parking on a driveway! 
Also a “ho spit al.” Why does English imply that someone named Al was created by an expectorating prostitute?
I’d go to the hospital too if I had a Pain In The Ass!
Why isn’t emordnilap a palindrome?
There are also a number of podcasts devoted to the history of English and/or the etymology of English words.
Why hasn’t the OPoster posted after one minute past the first post?
So, Thudlow Boink and Yllaria, why don’t you recommend some specific books and podcasts?
Because it’s a troll post. A post by a person who joined yesterday, posted this one question, and has never logged in again.
This obviously wasn’t a serious question. I thought so as soon as I read it. He’s probably laughing his ass off that he got so many serious answers.
It should have been deleted by the moderators soon after it was posted.
Nah, if it had gotten cornfielded we wouldn’t have gotten either to have fun with the responses or to obtain a bunch of references that some actual human beings may find interesting.
Some trolls are worth burning the bridge, some are not.
Parkway/driveway?