As for the library problem, I'm teaming up with Alex Gaynor, Hynek Schlawack, Donald Stufft and Christian Heimes to write a better cryptography library for Python: https://github.com/alex/cryptography
New contributors very welcome!
On the other side of the coin, I agree that cryptography education is very lacking. That's why I presented Crypto 101 last year at PyCon, which was an attempt at teaching just enough crypto in 45 minutes. Obviously, that's pretty near trying to square the circle: it's a best-effort attempt, but that's about it. (If you're still interested, the recording is available for free: http://pyvideo.org/video/1778/crypto-101)
That's why I'm also writing the book version of Crypto 101. Early draft stages right now, but getting there. After listening to tptacek say it so many times, I've come to agree: if you want to teach crypto well, you probably want a bunch of exercises that teach you how to break it. As a result, both the exercises and the text-adventure game I'm adding to the book rely on breaking real-world crypto: everything from bad password storage to MITMing SSL handshakes to stream compression :)
Additionally, a significant portion of the book will be devoted to when (i.e. rarely ;)) and how to write crypto. I would hope that your journey would've been a lot less painful if you had had access to the book. Perhaps for future programmers? :)
If you'd like to review, there's a reviewers mailing list, feel free to shoot me an e-mail explaining why you think you'd be a good reviewer, and I'll probably sign you up :)