Enforcing password strength

You could try LastPass, which is a cloud-based password manager with plugins for most browsers, and Yubikey, which is a hardware token emulating a keyboard. Set up LastPass to require use of Yubikey (and disable offline use), then set an easily typed password, on all keyboard variants, for LastPass - this will then send the password to all websites.

LastPass doesn't yet cover local applications on Linux, but you can copy/paste the password into Skype etc.