The problem with a strong passphrase is remembering it and entering it quickly. I can keep a few 12-14 characters passwords in my head, but that's about it.
I like the concept of passphrases, but they're too long to be manageable when you need to type them in a bunch of times.
I have used now a longer passphrase at work for my ldap login, and afer two days it didn't bothered my anymore with it's length.
(Passphrase was around the sime size as your first paragraph and was used for login, ssh, svn, git, email 82 and internal websites like bug trackers and wikis).
GPGTools (https://gpgtools.org/) can store your passphrase in the OSX keychain. It comes with GPGMail for Mail.app, which makes it very easy to encrypt email.
I like the concept of passphrases, but they're too long to be manageable when you need to type them in a bunch of times.